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Carbohydrate-Based Lactones: Synthesis and Applications

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Carbohydrates in Sustainable Development II

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 295))

Abstract

The synthesis and uses of different kinds of carbohydrate-based lactones are described. This group of compounds includes aldonolactones, other related monocyclic lactones and bicyclic systems. The latter can arise from uronic acids, carboxymethyl ethers or glycosides, or from C-branched sugars.

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Abbreviations

AAPDH:

2,2'-Azobis(2-amidinopropan) dihydrochloride

AD:

Asymmetric dihydroxylation

AIBN:

2,2'-Azobisisobutyronitrile

CMC:

Critical micellar concentration

CMG:

Carboxymethyl glycoside

CMGL:

Carboxymethyl glycoside 2-O-lactones

CSA:

Camphorsulfonic acid

DCC:

Dicyclohexylcarbodiimide

DEAD:

Diethyl azodicarboxylate

DIBAL-H:

Diisobutylaluminum hydride

DMAP:

4-(Dimethylamino)pyridine

DMJ:

1-Deoxymannojirimycin

DNJ:

Deoxynojirimycin

GABA:

γ-Aminobutyric acid

mCPBA:

m-Chloroperoxybenzoic acid

Ms:

Mesyl (methanesulfonyl)

MW:

Microwave irradiation

NBS:

N-Bromosuccinimide

NeuAc:

N-Acetyl neuraminic acid

NIS:

N-Iodosuccinimide

NMO:

N-Methylmorpholine N-oxide

Oct:

Octoate (2-ethylhexanoate)

PCC:

Pyridinium chlorochromate

PDC:

Pyridinium dichromate

Piv:

Pivaloyl

PMPOH:

p-Methoxyphenol

PPL:

Porcine pancreatic lipase

Py:

Pyridine

ROP:

Ring-opening polymerization

TBAF:

Tetrabutylammonium fluoride

TBDMS:

tert-Butyldimethylsilyl

Tf:

Trifluoromethanesulfonyl (triflyl)

TFA:

Trifluoroacetic acid

TFAA:

Trifluoroacetic anhydride

TMEDA:

N,N,N',N'-Tetramethyl-1,2-ethylenediamine

TMS:

Trimethylsilyl

TPAP:

Tetrapropylammonium perruthenate

Ts:

Tosyl, 4-toluenesulfonyl

References

  1. De Lederkremer RM, Varela O (1994) Adv Carbohydr Chem Biochem 50:125–209

    Article  Google Scholar 

  2. Lundt I (1997) Top Curr Chem 187:117–156

    Article  CAS  Google Scholar 

  3. Lundt I (2001) Top Curr Chem 215:177–191

    Article  CAS  Google Scholar 

  4. Lundt I (2003) Iminosugars, isoiminosugars, and carbasugars from activated carbohydrate lactones: efficient synthesis of biologically important compounds. In: Witzak ZJ, Tatsuta K (eds) Carbohydrate synthons in natural products chemistry: synthesis, functionalization and applications. ACS Symposium Series, vol 841. American Chemical Society, Washington, DC, pp 117–140

    Google Scholar 

  5. Fleet GWJ (1993) Sugar lactones as useful starting materials. In: Krohn K, Kirst HA, Maas H (eds) Antibiotics and antiviral compounds: chemical synthesis and modifications. VCH Verlagsgesellschaf, Weinheim, pp 333–342

    Google Scholar 

  6. Isbell HS (1963) Meth Carbohydr Chem 2:13–15

    CAS  Google Scholar 

  7. Madsen R (2008) Oxidation, reduction, and deoxygenation. In: Fraser-Reid BO, Tatsuta K, Thiem J (eds) Glycoscience chemistry and chemical biology. Springer, Berlin, p 181

    Google Scholar 

  8. Saburi M, Ishii Y, Kaji N, Aoi T, Sasaki I, Yoshikawa S, Uchida Y (1989) Chem Lett 563–566

    Google Scholar 

  9. Isaac I, Stasik I, Beaupère D, Uzan R (1995) Tetrahedron Lett 36:383–386

    Article  CAS  Google Scholar 

  10. Isaac I, Aizel G, Stasik I, Wadouachi A, Beaupère D (1998) Synlett 475–476

    Google Scholar 

  11. Luzzio FA (1998) Org React 53:12–21

    Google Scholar 

  12. Tidwell TT (1990) Synthesis 857–870

    Google Scholar 

  13. Tidwell TT (1990) Org React 39:297–572

    CAS  Google Scholar 

  14. Röper H (1991) Selective oxidations of D-glucose: chiral intermediates for industrial utilization. In: Lichtenthaler FW (ed) Carbohydrates as organic raw materials. VCH Verlagsgesellschaf, Weinheim

    Google Scholar 

  15. Besson M, Lahmer F, Gallezot P, Fuertes P, Flèche G (1995) J Catal 152:116–121

    Article  CAS  Google Scholar 

  16. Biella S, Prati L, Rossi M (2002) J Catal 206:242–247

    Article  CAS  Google Scholar 

  17. Wenkin M, Ruiz P, Delmon B, Devillers M (2002) J Mol Catal A: Chem 180:141–159

    Article  CAS  Google Scholar 

  18. Ramachandran S, Fontanille P, Pandey A, Larroche C (2006) Food Technol Biotechnol 44:185–195

    CAS  Google Scholar 

  19. Lichtenthaler FW (2006) The key sugars of biomass: availability, present non-food uses and potential future development lines. In: Kamm B, Gruber PR, Kamm M (eds) Biorefineries – industrial processes and products, status quo and future directions, vol 2. Wiley, Weinheim

    Google Scholar 

  20. Goebel M, Nothofer H-G, Ross G, Ugi I (1997) Tetrahedron 53:3123–3134

    Article  CAS  Google Scholar 

  21. Senni D, Praly J-P (1998) Synthetic Commun 28:433–441

    Article  CAS  Google Scholar 

  22. Bierenstiel M, Schlaf M (2004) Eur J Org Chem 2004:1474–1481

    Article  CAS  Google Scholar 

  23. Isbell HS, Frush HL (1933) Bur Stand J Res 11:649

    CAS  Google Scholar 

  24. Ahmed Md M, O‘Doherty GA (2005) Tetrahedron Lett 546:3015–3019

    Article  CAS  Google Scholar 

  25. Ahmed Md M, Berry BP, Hunter TJ, Tomcik DJ, O‘Doherty GA (2005) Org Lett 7:745–748

    Article  CAS  Google Scholar 

  26. Rao BV, Lahiri S (1996) J Carbohydr Chem 15:975–984

    Article  Google Scholar 

  27. Hi B, Moriarty RM, Penmasta R, Sharma V, Stanciuc G, Staszewski JP, Tuladhar SM, Walsh DA, Datla S, Krishnaswamy S (2006) Org Process Res Dev 10:484–486

    Article  CAS  Google Scholar 

  28. Hollingsworth RI, Song XZ (2007) Synlett 1247–1250

    Google Scholar 

  29. Johansen SK, Lundt I (1999) J Chem Soc Perkin Trans 1 24:3615–3622

    Article  Google Scholar 

  30. Wagner SH, Lundt I (2001) J Chem Soc Perkin Trans 1 8:780–788

    Article  Google Scholar 

  31. Johansen SK, Lundt I (2001) Eur J Org Chem 1129–1136

    Google Scholar 

  32. Long DD, Stetz RJE, Nash RJ, Marquess DG, Lloyd JD, Winters AL, Asano N, Fleet GWJ (1999) J Chem Soc Perkin Trans 1 901–908

    Google Scholar 

  33. Blériot Y, Simone MI, Wormald MR, Dwek RA, Watkin DJ, Fleet GWJ (2006) Tetrahedron Asymmetry 17:2276–2286

    Article  CAS  Google Scholar 

  34. Simone MI, Edwards AA, Tranter GE, Fleet GWJ (2008) Tetrahedron Asymmetry 19:2887–2894

    Article  CAS  Google Scholar 

  35. Kwoh D, Pocalyko DJ, Carchi AJ, Harirchian B, Hargiss LO, Wong TC (1995) Carbohydr Res 274:111–121

    Article  CAS  Google Scholar 

  36. Capderou M, Pale P (2004) C R Chimie 7:607–610

    Article  CAS  Google Scholar 

  37. Garésio F, Kardos N, Bonnevie C, Petit S, Luche J-L (2000) Green Chem 2:33–36

    Article  Google Scholar 

  38. Lalot J, Manier G, Stasik I, Demailly G, Beaupère D (2001) Carbohydr Res 335:55–61

    Article  CAS  Google Scholar 

  39. Chaveriat L, Stasik I, Demailly G, Beaupère D (2004) Carbohydr Res 339:1817–1821

    Article  CAS  Google Scholar 

  40. Lalot J, Stasik I, Demailly G, Beaupère D, Gode P (2004) J Colloid Interface Sci 73:604–610

    Article  CAS  Google Scholar 

  41. Lalot J, Stasik I, Demailly G, Beaupère D, Gode P (2003) J Therm Anal Calorim 74:77–83

    Article  CAS  Google Scholar 

  42. Fieser M, Fieser LF, Toromanoff E, Hirata Y, Heymann H, Tefft M, Bhattacharya S (1956) J Am Chem Soc 78:2825–2832

    Article  CAS  Google Scholar 

  43. Bastogne F, David C (1998) Colloids Surf A Physicochem Asp 139:311–320

    Article  CAS  Google Scholar 

  44. Baeyens-Volant D, Cuvelier P, Fornasier R, Szalai E, David C (1985) Mol Cryst Liq Cryst 128:277–286

    Article  CAS  Google Scholar 

  45. Baeyens-Volant D, Fornasier R, Szalai E, David C (1986) Mol Cryst Liq Cryst 135:93–110

    Article  CAS  Google Scholar 

  46. Loos M, Baeyens-Volant D, David C, Sigaud G, Achard MF (1990) J Colloid Interface Sci 138:128–133

    Article  CAS  Google Scholar 

  47. Loos M, Baeyens-Volant D, Szalai E, David C (1990) Makromol Chem 191:2917–2927

    Article  CAS  Google Scholar 

  48. Arevalo MJ, Avalos M, Babiano R, Cabanillas A, Cintas P, Jimenez JL, Palacios JC (2000) Tetrahedron Asymmetry 11:1985–1995

    Article  CAS  Google Scholar 

  49. Frankel DA, O’Brien F (1991) J Am Chem Soc 113:7436–7437

    Article  CAS  Google Scholar 

  50. Frankel DA, O’Brien F (1994) J Am Chem Soc 116:10057–10069

    Article  CAS  Google Scholar 

  51. Fuhrlop J-H, Blumtrtitt P, Lehmann C, Luger P (1991) J Am Chem Soc 113:7437–7439

    Article  Google Scholar 

  52. André C, Luger P, Bach R, Fuhrlop J-H (1995) Carbohydr Res 266:15–35

    Article  Google Scholar 

  53. Schmitzer A, Perez E, Rico-Lattes I, Lattes A (1999) Tetrahedron Lett 40:2947–2950

    Article  CAS  Google Scholar 

  54. Schmitzer A, Perez E, Rico-Lattes I, Lattes A, Rosca S (1999) Langmuir 15:4397–4403

    Article  CAS  Google Scholar 

  55. Schmitzer A, Franceschi I, Perez E, Rico-Lattes I, Lattes A, Thion L, Erard M, Vidal C (2001) J Am Chem Soc 123:5956–5961

    Article  CAS  Google Scholar 

  56. Reis RCN, Oda SC, De Almeida MV, Lourenço MCS, Vicente FRC, Barbosa NR, Trevizani R, Santos PLC, Le Hyaric M (2008) J Braz Chem Soc 19:1065–1072

    Article  CAS  Google Scholar 

  57. Varma AJ, Kennedy JF, Galgali P (2004) Carbohydr Polym 56:429–445

    Article  CAS  Google Scholar 

  58. Ladmiral V, Melia E, Haddleton DM (2004) Eur Polym J 40:431–449

    Article  CAS  Google Scholar 

  59. Spain SG, Gibson MI, Cameron NR (2007) J Polym Sci A Polym Chem 45:2059–2072

    Article  CAS  Google Scholar 

  60. Narain R, Jhurry D (2001) Polym Int 51:85–89

    Article  CAS  Google Scholar 

  61. Pinilla IM, Martínez MB, Galbis JA (2003) Carbohydr Res 338:549–555

    Article  CAS  Google Scholar 

  62. Haider AF, Williams CK (2008) J Polym Sci A Polym Chem 46:2891–2896

    Article  CAS  Google Scholar 

  63. Tang M, White AJP, Stevens MM, Williams CK (2009) Chem Commun 941–943

    Google Scholar 

  64. Tsutsumi N, Oya M, Sakai W (2004) Macromolecules 37:5971–5976

    Article  CAS  Google Scholar 

  65. Hunter DFA, Fleet GWJ (2003) Tetrahedron Asymmetry 14:3831–3839

    Article  CAS  Google Scholar 

  66. Kiely DE, Chen L, Lin T-H (2000) J Polym Sci A Polym Chem 38:594–603

    Article  CAS  Google Scholar 

  67. Styron SD, Kiely DE, Ponder G (2003) J Carbohydr Chem 22:123–142

    Article  CAS  Google Scholar 

  68. Chaveriat L, Stasik I, Demailly G, Beaupère D (2006) Tetrahedron Asymmetry 17:1349–1354

    Article  CAS  Google Scholar 

  69. Falentin C, Beaupère D, Demailly G, Stasik I (2007) Carbohydr Res 342:2807–2809

    Article  CAS  Google Scholar 

  70. Falentin C, Beaupère D, Demailly G, Stasik I (2008) Tetrahedron 64:9989–9991

    Article  CAS  Google Scholar 

  71. Lavaire S, Plantier-Royon R, Portella C (1998) US 5786469 (priority 1997, FR 2750134)

    Google Scholar 

  72. Du Y, Linhardt RJ (1998) Tetrahedron 54:9913–9959

    Article  CAS  Google Scholar 

  73. Nishikawa T, Adachi M, Isobe M (2008) C-Glycosylation. In: Fraser-Reid BO, Tatsuta K, Thiem J (eds) Glycoscience, chemistry and chemical biology. Springer, Heidelberg, pp 755–811

    Chapter  Google Scholar 

  74. Robina I, Vogel P (2008) Science of synthesis. Houben-Weyl Methods of Molecular Transformations, vol 37. Georg Thieme, Stuttgart, pp 645–845

    Google Scholar 

  75. Robina I, Vogel P (2005) Synthesis:675–702

    Google Scholar 

  76. Csuk R, Kühn M, Ströhl D (1997) Tetrahedron 53:1311–1322

    Article  CAS  Google Scholar 

  77. Schweizer F, Inazu T (2001) Org Lett 3:4115–4118

    Article  CAS  Google Scholar 

  78. Taillefumier C, Y (2004) Chem Rev 104:263–292

    Article  CAS  Google Scholar 

  79. Lakhrissi M, Chapleur Y (1994) J Org Chem 59:5752–5757

    Article  CAS  Google Scholar 

  80. Lakhrissi M, Chapleur Y (1996) Angew Chem Int Ed Engl 35:750–752

    Article  CAS  Google Scholar 

  81. Lakhrissi Y, Taillefumier C, Lakhrissi M, Chapleur Y (2000) Tetrahedron Asymmetry 11:417–421

    Article  CAS  Google Scholar 

  82. Lakhrissi M, Taillefumier C, Chaouch A, Didierjean C, Aubry A, Chapleur Y (1998) Tetrahedron Lett 39:6457–6460

    Article  CAS  Google Scholar 

  83. Taillefumier C, Lakhrissi YM, Lakhrissi M, Chapleur Y (2002) Tetrahedron Asymmetry 13:1707–1711

    Article  CAS  Google Scholar 

  84. Bourdon B, Corbet M, Fontaine P, Goekjian PG, Gueyrard D (2008) Tetrahedron Lett 49:747–749

    Article  CAS  Google Scholar 

  85. Yang W-B, Chang C-F, Wang S-H, Teo C-F, Lin C-H (2001) Tetrahedron Lett 42:4657–4660

    Article  CAS  Google Scholar 

  86. Nicotra F (1997) Top Curr Chem 187:55–83

    Article  CAS  Google Scholar 

  87. Bililign T, Griffith BR, Thorson JS (2005) Nat Prod Rep 22:742–760

    Article  CAS  Google Scholar 

  88. Lee DYW, He M (2005) Curr Top Med Chem 5:1333–1350

    Article  CAS  Google Scholar 

  89. Rauter AP, Lopes RG, Martins A (2007) Nat Prod Commun 2:1175–1196

    CAS  Google Scholar 

  90. Boyd VA, Drake BE, Sulikowski GA (1993) J Org Chem 58:3191–3193

    Article  CAS  Google Scholar 

  91. Li H, Procko K, Martin SF (2006) Tetrahedron Lett 47:3485–3488

    Article  CAS  Google Scholar 

  92. Hajkó J, Lipták A, Pozsgay V (1999) Carbohydr Res 321:116–120

    Article  Google Scholar 

  93. Takahashi H, Hitomi Y, Iwai Y, Ikegam S (2000) J Am Chem Soc 122:2995–3000

    Article  CAS  Google Scholar 

  94. Yang W-B, Patil SS, Tsai C-H, Lin C-H, Fang J-M (2002) Tetrahedron 58:253–259

    Article  CAS  Google Scholar 

  95. Asano N (2008) Azaglycomimetics: natural occurrence, biological activity, and application. In: Fraser-Reid BO, Tatsuta K, Thiem J (eds) Glycoscience, chemistry and chemical biology. Springer, Heidelberg, pp 1887–1911

    Chapter  Google Scholar 

  96. Stütz AE (ed) (1999) Iminosugars as glycosidase inhibitors: nojirimycin and beyond. Wiley, Weinheim

    Google Scholar 

  97. Song X, Hollingswortha RI (2007) Tetrahedron Lett 48:3115–3118

    Article  CAS  Google Scholar 

  98. Lundt I, Madsen R (1993) Synthesis 714–719

    Google Scholar 

  99. Lundt I, Madsen R (1993) Synthesis 720–724

    Google Scholar 

  100. Li H, Marcelo F, Bello C, Vogel P, Butters TD, Rauter AP, Zhang Y, Sollogoub M, Blériot Y (2009) Bioorg Med Chem 17:5598–5604, and references cited herein

    Article  CAS  Google Scholar 

  101. Gireaud L, Chaveriat L, Stasik I, Wadouachi A, Beaupère D (2006) Tetrahedron 62:7455–7458

    Article  CAS  Google Scholar 

  102. Jiao Y, Jie Fang Z, Jiang YH, Zheng BH, Cheng J (2008) Chin Chem Lett 19:795–796

    Article  CAS  Google Scholar 

  103. Zhou J, Zhang Y, Zhou X, Zhou J, Zhang L-H, Yea X-S, Zhang X-L (2008) Bioorg Med Chem 16:1605–1612

    Article  CAS  Google Scholar 

  104. Falentin C, Beaupère D, Demailly G, Stasik I (2009) Tetrahedron Lett 50:5364–5366

    Article  CAS  Google Scholar 

  105. Witczak ZJ (1999) Curr Med Chem 6:165–178

    CAS  Google Scholar 

  106. Witczak ZJ, Culhane JM (2005) Appl Microbiol Biotechnol 69:237–244

    Article  CAS  Google Scholar 

  107. Varela OP, Zunszain A (1993) J Org Chem 58:7860–7864

    Article  CAS  Google Scholar 

  108. Lalot J, Stasik I, Demailly G, Beaupère D (2003) Carbohydr Res 338:2241–2245

    Article  CAS  Google Scholar 

  109. Lalot J, Stasik I, Demailly G, Beaupère D (2002) Carbohydr Res 337:1411–1416

    Article  CAS  Google Scholar 

  110. Denmark SE, Regens CS, Kobayashi TJ (2007) Am Chem Soc 129:2774–2776, and references cited herein

    Article  CAS  Google Scholar 

  111. Rosenblum SB, Bihovsky R (1990) J Am Chem Soc 112:2746–2748

    Article  CAS  Google Scholar 

  112. Czernecki S, Perlat M-C (1991) J Org Chem 56:6289–6292

    Article  CAS  Google Scholar 

  113. McDonald FE, Zhu HYH, Holmquist CR (1995) J Am Chem Soc 117:6605–6606

    Article  CAS  Google Scholar 

  114. Yamamoto Y, Hashimoto T, Hattori K, Kikuchi M, Nishiyama H (2006) Org Lett 8:3565–3568

    Article  CAS  Google Scholar 

  115. Corsaro A, Pistarà V, Catelani G, D’Andrea F, Adamoa R, Chiacchioa MA (2006) Tetrahedron Lett 47:6591–6594, and references cited therein

    Article  CAS  Google Scholar 

  116. Ramana GV, Rao BV (2005) Tetrahedron Lett 46:3049–3051

    Article  CAS  Google Scholar 

  117. Shing TKM, Cheng HM (2007) J Org Chem 72:6610–6613

    Article  CAS  Google Scholar 

  118. Xavier NM, Rauter AP (2008) Carbohydr Res 343:1523–1539

    Article  CAS  Google Scholar 

  119. Rauter AP, Figueiredo JA, Ismael I, Pais MS, González AG, Bermejo JB, Diaz J (1987) J Carbohydr Chem 6:259–272

    Article  CAS  Google Scholar 

  120. Borges C, Almoster Ferreira MA, Rauter AP (1988) Biomed Environ Mass Spectrom 16:399–402

    Article  Google Scholar 

  121. Tripathi RP, Singh B, Bisht SS, Pandey J (2009) Curr Org Chem 13:99–122

    Article  CAS  Google Scholar 

  122. Ermolenko L, Sasaki NA, Potier P (2003) Helv Chim Acta 86:3578–3582

    Article  CAS  Google Scholar 

  123. Ermolenko L, Sasaki NA (2006) J Org Chem 71:693–703

    Article  CAS  Google Scholar 

  124. Vekemans JAJN, Franken GAM, Dapperns CWM, Godefroi EL, Chittenden GJF (1988) J Org Chem 53:627–633

    Article  CAS  Google Scholar 

  125. Horneman AM, Lundt I, Sotofte I (1995) Synlett 918–920

    Google Scholar 

  126. Schlessinger RH, Pettas LH (1998) J Org Chem 63:9098

    Article  Google Scholar 

  127. Mlynaski J, Banazzek A (1999) Tetrahedron 55:2785

    Article  Google Scholar 

  128. Kikely V, Plantia-Royon R, Portella C (2006) 1200–1204

    Google Scholar 

  129. Rollin P, Sinay P (1981) Carbohydr Res 98:139–142

    Article  CAS  Google Scholar 

  130. Bonadies F, Di Fabio R, Bonini C (1984) J Org Chem 49:1647–1649

    Article  CAS  Google Scholar 

  131. Rauter AP, Canda T, Justino J, Ismael MI, Figueiredo JA (2004) J Carbohydr Chem 23:239–251

    Article  CAS  Google Scholar 

  132. Yadav JS, Subba Reddy BV, Suresh Reddy C (2004) Tetrahedron Lett 45:4583–4585

    Article  CAS  Google Scholar 

  133. Jarglis P, Lichtenthaler FW (1982) Tetrahedron Lett 23:3781–3784

    Article  CAS  Google Scholar 

  134. Lichtenthaler FW, Klingler FD, Jarglis P (1984) Carbohydr Res 132:C1–C4

    Article  CAS  Google Scholar 

  135. Lichtenthaler FW, Rönninger S, Jarglis P (1989) Liebigs Ann Chem 1153–1161

    Google Scholar 

  136. Lichtenthaler FW, Werner B (1999) Carbohydr Res 319:47–54

    Article  CAS  Google Scholar 

  137. Chmielewski M, Jurczak J, Maciejewski S (1987) Carbohydr Res 165:111–115

    Article  CAS  Google Scholar 

  138. Hamann H-J, Höft E, Mostowicz D, Mishnev A, Urbañczyk-Lipkowska Z, Chmielewski M (1997) Tetrahedron 53:185–192

    Article  CAS  Google Scholar 

  139. Mostowicz D, Jurczak M, Hamann H-J, Höft E, Chmielewski M (1998) Eur J Org Chem 2617–2621

    Google Scholar 

  140. Panfil I, Mostowicz D, Chmielewski M (1999) Pol J Chem 73:1099–1110

    CAS  Google Scholar 

  141. Socha D, Jurczak M, Chmielewski M (1997) Tetrahedron 53:739–746

    Article  CAS  Google Scholar 

  142. Rabiczko J, Chmielewski M (1999) J Org Chem 64:1347–1351

    Article  CAS  Google Scholar 

  143. Panfil I, Urbañczyk-Lipkowska Z, Suwiñka K, Solecka J, Chmielewski M (2002) Tetrahedron 58:1199–1212

    Article  CAS  Google Scholar 

  144. Panfil I, Solecka J, Chmielewski M (2006) J Carbohydr Chem 25:673–684

    Article  CAS  Google Scholar 

  145. Paniczek K, Jurczak M, Solecka J, Urbaczyk-Lipkowska Z, Chmielewski M (2007) J Carbohydr Chem 26:195–211

    Article  CAS  Google Scholar 

  146. Stecko S, Frelek J, Chmielewski M (2009) Tetrahedron Asymmetry 20:1778–179

    Article  CAS  Google Scholar 

  147. Ferrieres V, Bertho JN, Plusquellec D (1998) Carbohydr Res 311:25–35

    Article  CAS  Google Scholar 

  148. Roussel M, Moutard S, Perly B, Lefeuvre M, Benvegnu T, Plusquellec D (2003) Carbohydr Res 338:375–378

    Article  CAS  Google Scholar 

  149. Salam MA, Isbell HS (1982) Carbohydr Res 101:255–261

    Article  CAS  Google Scholar 

  150. Bertho J-N, Coué A, Ewing DF, Goodby JW, Letellier P, Mackenzie G, Plusquellec D (1997) Carbohydr Res 300:341–346

    Article  CAS  Google Scholar 

  151. Berchel M, Lemiegre L, Trepouth S, Lambert O, Jeftic J, Benvegnu T (2008) Tetrahedron Lett 49:7419–7422

    Article  CAS  Google Scholar 

  152. Berchel M, Lemiegre L, Jeftic J, Benvegnu T (2008) Tetrahedron Lett 49:4690–4692

    Article  CAS  Google Scholar 

  153. Guilbot J, Benvegnu T, Legros N, Plusquellec D, Dedieu JC, Gulik A (2001) Langmuir 17:613–618

    Article  CAS  Google Scholar 

  154. Gaertzen O, Misske AM, Wolbers P, Hoffmann HMR (1999) Synlett 1041–1044

    Google Scholar 

  155. Gaertzen O, Misske AM, Wolbers P, Hoffmann HMR (1999) Tetrahedron Lett 40:6359–6363

    Article  CAS  Google Scholar 

  156. Polakova M, Pitt N, Tosin M, Murphy PV (2004) Angew Chem Int Ed 43:2518–2521

    Article  CAS  Google Scholar 

  157. Polakova M, Pitt N, Tosin M, Murphy PV (2007) Chem Eur J 13:902–909

    Article  CAS  Google Scholar 

  158. Rat S, Mathiron D, Michaud P, Kovensky J, Wadouachi A (2007) Tetrahedron 63:12424–12428

    Article  CAS  Google Scholar 

  159. Doyle D, Murphy PV (2008) Carbohydr Res 343:2535–2544

    Article  CAS  Google Scholar 

  160. Rauter AP, Weidmann H (1982) Liebigs Ann Chem 2231–2237

    Google Scholar 

  161. Pudelko M, Lindgren A, Tengel T, Reis CA, Elofsson M (2006) Kihlberg. J Org Biomol Chem 4:713–720

    Article  CAS  Google Scholar 

  162. Angata T, Varki A (2002) Chem Rev 102:439–469

    Article  CAS  Google Scholar 

  163. Pan GG, Melton LD (2006) Carbohydr Res 341:730–737

    Article  CAS  Google Scholar 

  164. Colombo R, Anastasia M, Rota P, Allevi P (2008) Chem Commun 5517–5519

    Google Scholar 

  165. Buali T, Bratosin D, Pons A, Montreuil J, Zanetta JP (2003) FEBS Lett 534:185–189

    Article  Google Scholar 

  166. Bratosin D, Pauli A, Moicean AD, Zanetta JP, Montreuil J (2007) Biochimie 89:355–359

    Article  CAS  Google Scholar 

  167. Gervay J, Ramamoorthy PS, Mamuya NN (1997) Tetrahedron 53:11039–11048

    Article  CAS  Google Scholar 

  168. Andersson L, Kenne L (2000) Carbohydr Res 329:257–268

    Article  CAS  Google Scholar 

  169. Andersson L, Kenne L (2003) Carbohydr Res 338:85–93

    Article  CAS  Google Scholar 

  170. Defossemont GM, Mincher DJ (2003) Carbohydr Res 338:563–565

    Article  CAS  Google Scholar 

  171. Yuan N, Kitagawa Y, Fukudome M, Fujita K (2007) Org Lett 9:4591–4594

    Article  CAS  Google Scholar 

  172. Queneau Y, Jarosz S, Lewandowski B, Fitremann J (2007) Adv Carbohydr Chem Biochem 61:217–292

    Article  CAS  Google Scholar 

  173. Queneau Y, Fitremann J, Trombotto S (2004) C R Chimie 7:177–188

    Article  CAS  Google Scholar 

  174. Brochette-Lemoine S, Joannard D, Descotes G, Bouchu A, Queneau Y (1999) J Mol Catal A Chem 150:31–36

    Article  CAS  Google Scholar 

  175. Lemoine S, Thomazeau C, Joannard D, Trombotto S, Descotes G, Bouchu A, Queneau Y (2000) Carbohydr Res 326:176–184

    Article  CAS  Google Scholar 

  176. Trombotto S, Violet-Courtens E, Cottier L, Queneau Y (2004) Top Catal 27:31–37

    Article  CAS  Google Scholar 

  177. Weidenhagen R, Lorenz S (1957) Angew Chem 69:641–641

    Article  CAS  Google Scholar 

  178. Schiweck H, Munir M, Rapp KM, Schneider B, Vogel M (1991) New developments in the use of sucrose as an industrial bulk chemical. In: Lichtenthaler FW (ed) Carbohydrates as organic raw materials. VCH, Weinheim, pp 57–94

    Google Scholar 

  179. Lichtenthaler FW, Peters S (2004) C R Chimie 7:65–90

    Article  CAS  Google Scholar 

  180. Lichtenthaler FW (1998) Carbohydr Res 313:69–89

    Article  CAS  Google Scholar 

  181. Lichtenthaler FW (2002) Acc Chem Res 35:728–737

    Article  CAS  Google Scholar 

  182. Lichtenthaler FW, Klimesch R, Muller V, Kunz M (1993) Liebigs Ann Chem 975–980

    Google Scholar 

  183. Trombotto S, Bouchu A, Descotes G, Queneau Y (2000) Tetrahedron Lett 41:8273–8277

    Article  CAS  Google Scholar 

  184. Trombotto S, Danel M, Fitremann J, Bouchu A, Queneau Y (2003) J Org Chem 68:6672–6678

    Article  CAS  Google Scholar 

  185. Pierre R, Chambert S, Alirachedi F, Danel M, Trombotto S, Doutheau A, Queneau Y (2008) C R Chimie 11:61–66

    Article  CAS  Google Scholar 

  186. Listkowski A, Ing P, Cheaib R, Chambert S, Doutheau A, Queneau Y (2007) Tetrahedron:Asymmetry 18:220–2210

    Article  CAS  Google Scholar 

  187. Cheaib R, Listkowski A, Chambert S, Doutheau A, Queneau Y (2008) Tetrahedron Asymmetry 19:1919–1933

    Article  CAS  Google Scholar 

  188. Dean B, Oguchi H, Cai S, Otsuji E, Tashiro K, Hakomori S, Toyokuni T (1993) Carbohydr Res 245:175–192

    Article  CAS  Google Scholar 

  189. Shiozaki M, Shimozato R, Watanabe Y, Mochizuki T (2006) JP 2006008539, Chem Abs 144:101029

    Google Scholar 

  190. Schmidt RR (1996) In: Kahn SH, O’Neill RA (eds) Modern methods in carbohydrate synthesis. Harwood Academic, Amsterdam, pp 20–54

    Google Scholar 

  191. Schmidt RR (1986) Angew Chem 25:213–236

    Article  Google Scholar 

  192. Klotz W, Schmidt RR (1993) Liebigs Ann Chem 683–690

    Google Scholar 

  193. Le Chevalier A, Pierre R, Kanso R, Chambert S, Doutheau A, Queneau Y (2006) Tetrahedron Lett 47:2431–2434

    Article  CAS  Google Scholar 

  194. Sol V, Charmot A, Krausz P, Trombotto S, Queneau Y (2006) J Carbohydr Chem 25:345–360

    Article  CAS  Google Scholar 

  195. Ménard F, Sol V, Ringot C, Granet R, Alves S, Le Morvan C, Queneau Y, Ono N, Krausz P (2009) Bioorg Med Chem 17:7647–7657

    Article  CAS  Google Scholar 

  196. Chambert S, Doutheau A, Queneau Y, Cowling SJ, Goodby JW, Mackenzie G (2007) J Carbohydr Chem 26:27–39

    Article  CAS  Google Scholar 

  197. Barsu C, Cheaib R, Chambert S, Queneau Y, Maury OL, Cottet D, Wege H, Douady J, Bretonnière Y, Andraud C (2010) Org Biomol Chem 8:142–150

    Article  CAS  Google Scholar 

  198. Queneau Y, Gagnaire J, West JJ, Mackenzie G, Goodby JW (2001) J Mater Chem 11:2839–2844

    Article  CAS  Google Scholar 

  199. Molinier VP, Kouwer HJ, Queneau Y, Fitremann J, Mackenzie G, Goodby JW (2003) Chem Commun 2860–2861

    Google Scholar 

  200. Kouwer MVP, JJ FJ, Bouchu A, Mackenzie G, Queneau Y, Goodby JW (2006) Chem Eur J 12:3547–3557

    Article  CAS  Google Scholar 

  201. Molinier V, Kouwer PJJ, Fitremann J, Bouchu A, Mackenzie G, Queneau Y, Goodby JW (2007) Chem Eur J 13:1763–1775

    Article  CAS  Google Scholar 

  202. Goodby JW, Gortz V, Cowling SJ, Mackenzie G, Martin P, Plusquellec D, Benvegnu T, Boullanger P, Lafont D, Queneau Y, Chambert S, Fitremann J (2007) Chem Soc Rev 36:1971–2032

    Article  CAS  Google Scholar 

  203. Molinier V, Fenet B, Fitremann J, Bouchu A, Queneau Y (2005) J Colloid Interface Sci 286:360–368

    Article  CAS  Google Scholar 

  204. Queneau Y, Chambert S, Besset C, Cheaib R (2008) Carbohydr Res 343:1999–2009

    Article  CAS  Google Scholar 

  205. Ali Rachedi F, Chambert S, Ferkous F, Queneau Y, Cowling SJ, Goodby JW (2009) Chem Commun 6355–6357

    Google Scholar 

  206. Xavier NM, Chambert S, Rauter AP, Queneau Y unpublished

    Google Scholar 

  207. Araújo AC, Nicotra F, Costa B, Giagnoni G, Cipolla L (2008) Carbohydr Res 343:1840–1848

    Article  CAS  Google Scholar 

  208. Velazquez S, Jimeno ML, Huss S, Balzarini J, Camarasa M-J (1994) J Org Chem 59:7661–7670

    Article  CAS  Google Scholar 

  209. Gregori A, Alibés R, Bourdelande JL, Font J (1998) Tetrahedron Lett 39:6963–6966

    Article  CAS  Google Scholar 

  210. Alibés R, Bourdelande JL, Gregori A, Font J, Rustullet A, Parella T (2003) J Carbohydr Chem 22:501–511

    Article  CAS  Google Scholar 

  211. Yu M, Lynch V, Pagenkopf BL (2001) Org Lett 3:2563–2566

    Article  CAS  Google Scholar 

  212. Rauter A, Ferreira M, Duarte T, Piedade F, Silva M, Santos H (2000) Carbohydr Res 325:1–15

    Article  CAS  Google Scholar 

  213. Rauter AP, Oliveira O, Canda T, Leroi E, Ferreira H, Ferreira MJ, Ascenso JA (2002) J Carbohydr Chem 21:257–274

    Article  CAS  Google Scholar 

  214. Yu M, Pagenkopf BL (2003) Tetrahedron 59:2765–2771

    Article  CAS  Google Scholar 

  215. Haveli SD, Sridhar PR, Suguna P, Chandrasekaran S (2007) Org Lett 9:1331–1334

    Article  CAS  Google Scholar 

  216. Yin J, Linker T (2009) Chem Eur J 15:49–52

    Article  CAS  Google Scholar 

  217. Yin J, Sommermann T, Linker T (2007) Chem Eur J 13:10152–10167

    Article  CAS  Google Scholar 

  218. de Oliveira RB, Alves RJ, de Souza JD, Prado MAF (2003) J Braz Chem Soc 14:442–448

    Article  Google Scholar 

  219. Rungeler P, Castro V, Mora G, Goren N, Vichnewski W, Pahl HL, Merfort I, Schmidt TJ (1999) Bioorg Med Chem 7:2343–2352

    Article  CAS  Google Scholar 

  220. Oh S, Jeong IH, Shin W-S, Wang Q, Lee S (2006) Bioorg Med Chem Lett 16:1656–1659

    Article  CAS  Google Scholar 

  221. Li D-H, Zhu T-J, Liu H-B, Fang Y-C, Gu Q-Q, Zhu W-M (2006) Arch Pharm Res 29:624–626

    Article  CAS  Google Scholar 

  222. Cateni F, Zilic J, Zacchigna M, Bonivento P, Frausin F, Scarcia V (2006) Eur J Med Chem 41:192–200

    Article  CAS  Google Scholar 

  223. Prasad KR, Gholap SL (2008) J Org Chem 73:2–11

    Article  CAS  Google Scholar 

  224. Mereyala HB, Joe M (2001) Curr Med Chem AntiCancer Agents 1:293–300

    Article  CAS  Google Scholar 

  225. Gesson J-P, Jacquesy JC, Mondon M (1989) Tetrahedron 45:2627–2640

    Article  CAS  Google Scholar 

  226. Bennet M, Gill GB, Pattenden G, Shuker AJ, Stapleton A (1991) J Chem Soc Perkin Trans 1:929–937

    Google Scholar 

  227. Rychlik M, Schieberle P (1998) J Agric Food Chem 46:5163–5169

    Article  CAS  Google Scholar 

  228. Liu H-M, Zhang F, Zhang J, Shi L (2003) Carbohydr Res 338:1737–1743

    Article  CAS  Google Scholar 

  229. Xavier NM, Rauter AP (2007) Org Lett 9:3339–3341

    Article  CAS  Google Scholar 

  230. Xavier NM, Silva S, Madeira PJA, Florêncio MH, Silva FVM, Justino J, Thiem J, Rauter AP (2008) Eur J Org Chem 2008:6134–6143

    Article  CAS  Google Scholar 

  231. Xavier NM, Madeira PJA, Florêncio MH, Rauter AP (2009) Eur J Org Chem 2009:4983–4991

    Article  CAS  Google Scholar 

  232. Zhang J, Clive DLJ (1999) J Org Chem 64:770–779

    Article  CAS  Google Scholar 

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Acknowledgments

The authors acknowledge the following institutions for financial support: FCT (for the support of the project POCI-PPCDT/QUI/59672/2004 and for the PhD grant SFRH/BD/39251/2007), CPU/CRUP (for a joint Portuguese-French research program), MESER, and CNRS. Dr. Sylvie Moebs is gratefully acknowledged for her helpful discussions during the preparation of the manuscript.

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Authors and Affiliations

  1. Centro de Química e Bioquímica, Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade de Lisboa, Ed. C8, 5° Piso, Campo Grande, 1749-016, Lisboa, Portugal

    Nuno M. Xavier & Amélia P. Rauter

  2. Laboratoire de Chimie Organique, INSA Lyon, Bâtiment J. Verne, 20 av A. Einstein, 69621, Villeurbanne, France

    Nuno M. Xavier & Yves Queneau

  3. Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, UMR 5246, Université Lyon 1, Bâtiment CPE, 43 bd du 11 novembre 1918, 69622, Villeurbanne, France

    Nuno M. Xavier & Yves Queneau

  4. Université de Lyon, INSA-Lyon, CNRS, CPE-Lyon, Villeurbanne, France

    Nuno M. Xavier & Yves Queneau

Authors
  1. Nuno M. Xavier
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  2. Amélia P. Rauter
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  3. Yves Queneau
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Correspondence to Yves Queneau .

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Editors and Affiliations

  1. Fac. Ciências, Depto. Química e Bioquímica, Universidade de Lisboa, Campo Grande, Lisboa, 1749-016, Portugal

    Amélia P. Rauter

  2. , EPFL ICMB LGSA, Swiss Federal Inst. of Technology, Bat BCH, Lausanne, 1015, Switzerland

    Pierre Vogel

  3. Labo. Chimie Organique (LCO), INSA Lyon, av. Albert Einstein 20, Villeurbanne CX, 69621, France

    Yves Queneau

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Xavier, N.M., Rauter, A.P., Queneau, Y. (2010). Carbohydrate-Based Lactones: Synthesis and Applications. In: Rauter, A., Vogel, P., Queneau, Y. (eds) Carbohydrates in Sustainable Development II. Topics in Current Chemistry, vol 295. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2010_61

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