Carbohydrate-Based Lactones: Synthesis and Applications

  • Nuno M. Xavier
  • Amélia P. Rauter
  • Yves QueneauEmail author
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 295)


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.


Aldonolactones Bicyclic lactones Gluconolactone Sugar lactones Synthons Uronic acids 



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


Asymmetric dihydroxylation




Critical micellar concentration


Carboxymethyl glycoside


Carboxymethyl glycoside 2-O-lactones


Camphorsulfonic acid




Diethyl azodicarboxylate


Diisobutylaluminum hydride








γ-Aminobutyric acid


m-Chloroperoxybenzoic acid


Mesyl (methanesulfonyl)


Microwave irradiation




N-Acetyl neuraminic acid




N-Methylmorpholine N-oxide


Octoate (2-ethylhexanoate)


Pyridinium chlorochromate


Pyridinium dichromate






Porcine pancreatic lipase




Ring-opening polymerization


Tetrabutylammonium fluoride




Trifluoromethanesulfonyl (triflyl)


Trifluoroacetic acid


Trifluoroacetic anhydride






Tetrapropylammonium perruthenate


Tosyl, 4-toluenesulfonyl



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.


  1. 1.
    De Lederkremer RM, Varela O (1994) Adv Carbohydr Chem Biochem 50:125–209CrossRefGoogle Scholar
  2. 2.
    Lundt I (1997) Top Curr Chem 187:117–156CrossRefGoogle Scholar
  3. 3.
    Lundt I (2001) Top Curr Chem 215:177–191CrossRefGoogle Scholar
  4. 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 117–140Google Scholar
  5. 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 333–342Google Scholar
  6. 6.
    Isbell HS (1963) Meth Carbohydr Chem 2:13–15Google Scholar
  7. 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 181Google Scholar
  8. 8.
    Saburi M, Ishii Y, Kaji N, Aoi T, Sasaki I, Yoshikawa S, Uchida Y (1989) Chem Lett 563–566Google Scholar
  9. 9.
    Isaac I, Stasik I, Beaupère D, Uzan R (1995) Tetrahedron Lett 36:383–386CrossRefGoogle Scholar
  10. 10.
    Isaac I, Aizel G, Stasik I, Wadouachi A, Beaupère D (1998) Synlett 475–476Google Scholar
  11. 11.
    Luzzio FA (1998) Org React 53:12–21Google Scholar
  12. 12.
    Tidwell TT (1990) Synthesis 857–870Google Scholar
  13. 13.
    Tidwell TT (1990) Org React 39:297–572Google Scholar
  14. 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, WeinheimGoogle Scholar
  15. 15.
    Besson M, Lahmer F, Gallezot P, Fuertes P, Flèche G (1995) J Catal 152:116–121CrossRefGoogle Scholar
  16. 16.
    Biella S, Prati L, Rossi M (2002) J Catal 206:242–247CrossRefGoogle Scholar
  17. 17.
    Wenkin M, Ruiz P, Delmon B, Devillers M (2002) J Mol Catal A: Chem 180:141–159CrossRefGoogle Scholar
  18. 18.
    Ramachandran S, Fontanille P, Pandey A, Larroche C (2006) Food Technol Biotechnol 44:185–195Google Scholar
  19. 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, WeinheimGoogle Scholar
  20. 20.
    Goebel M, Nothofer H-G, Ross G, Ugi I (1997) Tetrahedron 53:3123–3134CrossRefGoogle Scholar
  21. 21.
    Senni D, Praly J-P (1998) Synthetic Commun 28:433–441CrossRefGoogle Scholar
  22. 22.
    Bierenstiel M, Schlaf M (2004) Eur J Org Chem 2004:1474–1481CrossRefGoogle Scholar
  23. 23.
    Isbell HS, Frush HL (1933) Bur Stand J Res 11:649Google Scholar
  24. 24.
    Ahmed Md M, O‘Doherty GA (2005) Tetrahedron Lett 546:3015–3019CrossRefGoogle Scholar
  25. 25.
    Ahmed Md M, Berry BP, Hunter TJ, Tomcik DJ, O‘Doherty GA (2005) Org Lett 7:745–748CrossRefGoogle Scholar
  26. 26.
    Rao BV, Lahiri S (1996) J Carbohydr Chem 15:975–984CrossRefGoogle Scholar
  27. 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 10:484–486CrossRefGoogle Scholar
  28. 28.
    Hollingsworth RI, Song XZ (2007) Synlett 1247–1250Google Scholar
  29. 29.
    Johansen SK, Lundt I (1999) J Chem Soc Perkin Trans 1 24:3615–3622CrossRefGoogle Scholar
  30. 30.
    Wagner SH, Lundt I (2001) J Chem Soc Perkin Trans 1 8:780–788CrossRefGoogle Scholar
  31. 31.
    Johansen SK, Lundt I (2001) Eur J Org Chem 1129–1136Google Scholar
  32. 32.
    Long DD, Stetz RJE, Nash RJ, Marquess DG, Lloyd JD, Winters AL, Asano N, Fleet GWJ (1999) J Chem Soc Perkin Trans 1 901–908Google Scholar
  33. 33.
    Blériot Y, Simone MI, Wormald MR, Dwek RA, Watkin DJ, Fleet GWJ (2006) Tetrahedron Asymmetry 17:2276–2286CrossRefGoogle Scholar
  34. 34.
    Simone MI, Edwards AA, Tranter GE, Fleet GWJ (2008) Tetrahedron Asymmetry 19:2887–2894CrossRefGoogle Scholar
  35. 35.
    Kwoh D, Pocalyko DJ, Carchi AJ, Harirchian B, Hargiss LO, Wong TC (1995) Carbohydr Res 274:111–121CrossRefGoogle Scholar
  36. 36.
    Capderou M, Pale P (2004) C R Chimie 7:607–610CrossRefGoogle Scholar
  37. 37.
    Garésio F, Kardos N, Bonnevie C, Petit S, Luche J-L (2000) Green Chem 2:33–36CrossRefGoogle Scholar
  38. 38.
    Lalot J, Manier G, Stasik I, Demailly G, Beaupère D (2001) Carbohydr Res 335:55–61CrossRefGoogle Scholar
  39. 39.
    Chaveriat L, Stasik I, Demailly G, Beaupère D (2004) Carbohydr Res 339:1817–1821CrossRefGoogle Scholar
  40. 40.
    Lalot J, Stasik I, Demailly G, Beaupère D, Gode P (2004) J Colloid Interface Sci 73:604–610CrossRefGoogle Scholar
  41. 41.
    Lalot J, Stasik I, Demailly G, Beaupère D, Gode P (2003) J Therm Anal Calorim 74:77–83CrossRefGoogle Scholar
  42. 42.
    Fieser M, Fieser LF, Toromanoff E, Hirata Y, Heymann H, Tefft M, Bhattacharya S (1956) J Am Chem Soc 78:2825–2832CrossRefGoogle Scholar
  43. 43.
    Bastogne F, David C (1998) Colloids Surf A Physicochem Asp 139:311–320CrossRefGoogle Scholar
  44. 44.
    Baeyens-Volant D, Cuvelier P, Fornasier R, Szalai E, David C (1985) Mol Cryst Liq Cryst 128:277–286CrossRefGoogle Scholar
  45. 45.
    Baeyens-Volant D, Fornasier R, Szalai E, David C (1986) Mol Cryst Liq Cryst 135:93–110CrossRefGoogle Scholar
  46. 46.
    Loos M, Baeyens-Volant D, David C, Sigaud G, Achard MF (1990) J Colloid Interface Sci 138:128–133CrossRefGoogle Scholar
  47. 47.
    Loos M, Baeyens-Volant D, Szalai E, David C (1990) Makromol Chem 191:2917–2927CrossRefGoogle Scholar
  48. 48.
    Arevalo MJ, Avalos M, Babiano R, Cabanillas A, Cintas P, Jimenez JL, Palacios JC (2000) Tetrahedron Asymmetry 11:1985–1995CrossRefGoogle Scholar
  49. 49.
    Frankel DA, O’Brien F (1991) J Am Chem Soc 113:7436–7437CrossRefGoogle Scholar
  50. 50.
    Frankel DA, O’Brien F (1994) J Am Chem Soc 116:10057–10069CrossRefGoogle Scholar
  51. 51.
    Fuhrlop J-H, Blumtrtitt P, Lehmann C, Luger P (1991) J Am Chem Soc 113:7437–7439CrossRefGoogle Scholar
  52. 52.
    André C, Luger P, Bach R, Fuhrlop J-H (1995) Carbohydr Res 266:15–35CrossRefGoogle Scholar
  53. 53.
    Schmitzer A, Perez E, Rico-Lattes I, Lattes A (1999) Tetrahedron Lett 40:2947–2950CrossRefGoogle Scholar
  54. 54.
    Schmitzer A, Perez E, Rico-Lattes I, Lattes A, Rosca S (1999) Langmuir 15:4397–4403CrossRefGoogle Scholar
  55. 55.
    Schmitzer A, Franceschi I, Perez E, Rico-Lattes I, Lattes A, Thion L, Erard M, Vidal C (2001) J Am Chem Soc 123:5956–5961CrossRefGoogle Scholar
  56. 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 19:1065–1072CrossRefGoogle Scholar
  57. 57.
    Varma AJ, Kennedy JF, Galgali P (2004) Carbohydr Polym 56:429–445CrossRefGoogle Scholar
  58. 58.
    Ladmiral V, Melia E, Haddleton DM (2004) Eur Polym J 40:431–449CrossRefGoogle Scholar
  59. 59.
    Spain SG, Gibson MI, Cameron NR (2007) J Polym Sci A Polym Chem 45:2059–2072CrossRefGoogle Scholar
  60. 60.
    Narain R, Jhurry D (2001) Polym Int 51:85–89CrossRefGoogle Scholar
  61. 61.
    Pinilla IM, Martínez MB, Galbis JA (2003) Carbohydr Res 338:549–555CrossRefGoogle Scholar
  62. 62.
    Haider AF, Williams CK (2008) J Polym Sci A Polym Chem 46:2891–2896CrossRefGoogle Scholar
  63. 63.
    Tang M, White AJP, Stevens MM, Williams CK (2009) Chem Commun 941–943Google Scholar
  64. 64.
    Tsutsumi N, Oya M, Sakai W (2004) Macromolecules 37:5971–5976CrossRefGoogle Scholar
  65. 65.
    Hunter DFA, Fleet GWJ (2003) Tetrahedron Asymmetry 14:3831–3839CrossRefGoogle Scholar
  66. 66.
    Kiely DE, Chen L, Lin T-H (2000) J Polym Sci A Polym Chem 38:594–603CrossRefGoogle Scholar
  67. 67.
    Styron SD, Kiely DE, Ponder G (2003) J Carbohydr Chem 22:123–142CrossRefGoogle Scholar
  68. 68.
    Chaveriat L, Stasik I, Demailly G, Beaupère D (2006) Tetrahedron Asymmetry 17:1349–1354CrossRefGoogle Scholar
  69. 69.
    Falentin C, Beaupère D, Demailly G, Stasik I (2007) Carbohydr Res 342:2807–2809CrossRefGoogle Scholar
  70. 70.
    Falentin C, Beaupère D, Demailly G, Stasik I (2008) Tetrahedron 64:9989–9991CrossRefGoogle Scholar
  71. 71.
    Lavaire S, Plantier-Royon R, Portella C (1998) US 5786469 (priority 1997, FR 2750134)Google Scholar
  72. 72.
    Du Y, Linhardt RJ (1998) Tetrahedron 54:9913–9959CrossRefGoogle Scholar
  73. 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 755–811CrossRefGoogle Scholar
  74. 74.
    Robina I, Vogel P (2008) Science of synthesis. Houben-Weyl Methods of Molecular Transformations, vol 37. Georg Thieme, Stuttgart, pp 645–845Google Scholar
  75. 75.
    Robina I, Vogel P (2005) Synthesis:675–702Google Scholar
  76. 76.
    Csuk R, Kühn M, Ströhl D (1997) Tetrahedron 53:1311–1322CrossRefGoogle Scholar
  77. 77.
    Schweizer F, Inazu T (2001) Org Lett 3:4115–4118CrossRefGoogle Scholar
  78. 78.
    Taillefumier C, Y (2004) Chem Rev 104:263–292CrossRefGoogle Scholar
  79. 79.
    Lakhrissi M, Chapleur Y (1994) J Org Chem 59:5752–5757CrossRefGoogle Scholar
  80. 80.
    Lakhrissi M, Chapleur Y (1996) Angew Chem Int Ed Engl 35:750–752CrossRefGoogle Scholar
  81. 81.
    Lakhrissi Y, Taillefumier C, Lakhrissi M, Chapleur Y (2000) Tetrahedron Asymmetry 11:417–421CrossRefGoogle Scholar
  82. 82.
    Lakhrissi M, Taillefumier C, Chaouch A, Didierjean C, Aubry A, Chapleur Y (1998) Tetrahedron Lett 39:6457–6460CrossRefGoogle Scholar
  83. 83.
    Taillefumier C, Lakhrissi YM, Lakhrissi M, Chapleur Y (2002) Tetrahedron Asymmetry 13:1707–1711CrossRefGoogle Scholar
  84. 84.
    Bourdon B, Corbet M, Fontaine P, Goekjian PG, Gueyrard D (2008) Tetrahedron Lett 49:747–749CrossRefGoogle Scholar
  85. 85.
    Yang W-B, Chang C-F, Wang S-H, Teo C-F, Lin C-H (2001) Tetrahedron Lett 42:4657–4660CrossRefGoogle Scholar
  86. 86.
    Nicotra F (1997) Top Curr Chem 187:55–83CrossRefGoogle Scholar
  87. 87.
    Bililign T, Griffith BR, Thorson JS (2005) Nat Prod Rep 22:742–760CrossRefGoogle Scholar
  88. 88.
    Lee DYW, He M (2005) Curr Top Med Chem 5:1333–1350CrossRefGoogle Scholar
  89. 89.
    Rauter AP, Lopes RG, Martins A (2007) Nat Prod Commun 2:1175–1196Google Scholar
  90. 90.
    Boyd VA, Drake BE, Sulikowski GA (1993) J Org Chem 58:3191–3193CrossRefGoogle Scholar
  91. 91.
    Li H, Procko K, Martin SF (2006) Tetrahedron Lett 47:3485–3488CrossRefGoogle Scholar
  92. 92.
    Hajkó J, Lipták A, Pozsgay V (1999) Carbohydr Res 321:116–120CrossRefGoogle Scholar
  93. 93.
    Takahashi H, Hitomi Y, Iwai Y, Ikegam S (2000) J Am Chem Soc 122:2995–3000CrossRefGoogle Scholar
  94. 94.
    Yang W-B, Patil SS, Tsai C-H, Lin C-H, Fang J-M (2002) Tetrahedron 58:253–259CrossRefGoogle Scholar
  95. 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 1887–1911CrossRefGoogle Scholar
  96. 96.
    Stütz AE (ed) (1999) Iminosugars as glycosidase inhibitors: nojirimycin and beyond. Wiley, WeinheimGoogle Scholar
  97. 97.
    Song X, Hollingswortha RI (2007) Tetrahedron Lett 48:3115–3118CrossRefGoogle Scholar
  98. 98.
    Lundt I, Madsen R (1993) Synthesis 714–719Google Scholar
  99. 99.
    Lundt I, Madsen R (1993) Synthesis 720–724Google Scholar
  100. 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 hereinCrossRefGoogle Scholar
  101. 101.
    Gireaud L, Chaveriat L, Stasik I, Wadouachi A, Beaupère D (2006) Tetrahedron 62:7455–7458CrossRefGoogle Scholar
  102. 102.
    Jiao Y, Jie Fang Z, Jiang YH, Zheng BH, Cheng J (2008) Chin Chem Lett 19:795–796CrossRefGoogle Scholar
  103. 103.
    Zhou J, Zhang Y, Zhou X, Zhou J, Zhang L-H, Yea X-S, Zhang X-L (2008) Bioorg Med Chem 16:1605–1612CrossRefGoogle Scholar
  104. 104.
    Falentin C, Beaupère D, Demailly G, Stasik I (2009) Tetrahedron Lett 50:5364–5366CrossRefGoogle Scholar
  105. 105.
    Witczak ZJ (1999) Curr Med Chem 6:165–178Google Scholar
  106. 106.
    Witczak ZJ, Culhane JM (2005) Appl Microbiol Biotechnol 69:237–244CrossRefGoogle Scholar
  107. 107.
    Varela OP, Zunszain A (1993) J Org Chem 58:7860–7864CrossRefGoogle Scholar
  108. 108.
    Lalot J, Stasik I, Demailly G, Beaupère D (2003) Carbohydr Res 338:2241–2245CrossRefGoogle Scholar
  109. 109.
    Lalot J, Stasik I, Demailly G, Beaupère D (2002) Carbohydr Res 337:1411–1416CrossRefGoogle Scholar
  110. 110.
    Denmark SE, Regens CS, Kobayashi TJ (2007) Am Chem Soc 129:2774–2776, and references cited hereinCrossRefGoogle Scholar
  111. 111.
    Rosenblum SB, Bihovsky R (1990) J Am Chem Soc 112:2746–2748CrossRefGoogle Scholar
  112. 112.
    Czernecki S, Perlat M-C (1991) J Org Chem 56:6289–6292CrossRefGoogle Scholar
  113. 113.
    McDonald FE, Zhu HYH, Holmquist CR (1995) J Am Chem Soc 117:6605–6606CrossRefGoogle Scholar
  114. 114.
    Yamamoto Y, Hashimoto T, Hattori K, Kikuchi M, Nishiyama H (2006) Org Lett 8:3565–3568CrossRefGoogle Scholar
  115. 115.
    Corsaro A, Pistarà V, Catelani G, D’Andrea F, Adamoa R, Chiacchioa MA (2006) Tetrahedron Lett 47:6591–6594, and references cited thereinCrossRefGoogle Scholar
  116. 116.
    Ramana GV, Rao BV (2005) Tetrahedron Lett 46:3049–3051CrossRefGoogle Scholar
  117. 117.
    Shing TKM, Cheng HM (2007) J Org Chem 72:6610–6613CrossRefGoogle Scholar
  118. 118.
    Xavier NM, Rauter AP (2008) Carbohydr Res 343:1523–1539CrossRefGoogle Scholar
  119. 119.
    Rauter AP, Figueiredo JA, Ismael I, Pais MS, González AG, Bermejo JB, Diaz J (1987) J Carbohydr Chem 6:259–272CrossRefGoogle Scholar
  120. 120.
    Borges C, Almoster Ferreira MA, Rauter AP (1988) Biomed Environ Mass Spectrom 16:399–402CrossRefGoogle Scholar
  121. 121.
    Tripathi RP, Singh B, Bisht SS, Pandey J (2009) Curr Org Chem 13:99–122CrossRefGoogle Scholar
  122. 122.
    Ermolenko L, Sasaki NA, Potier P (2003) Helv Chim Acta 86:3578–3582CrossRefGoogle Scholar
  123. 123.
    Ermolenko L, Sasaki NA (2006) J Org Chem 71:693–703CrossRefGoogle Scholar
  124. 124.
    Vekemans JAJN, Franken GAM, Dapperns CWM, Godefroi EL, Chittenden GJF (1988) J Org Chem 53:627–633CrossRefGoogle Scholar
  125. 125.
    Horneman AM, Lundt I, Sotofte I (1995) Synlett 918–920Google Scholar
  126. 126.
    Schlessinger RH, Pettas LH (1998) J Org Chem 63:9098CrossRefGoogle Scholar
  127. 127.
    Mlynaski J, Banazzek A (1999) Tetrahedron 55:2785CrossRefGoogle Scholar
  128. 128.
    Kikely V, Plantia-Royon R, Portella C (2006) 1200–1204Google Scholar
  129. 129.
    Rollin P, Sinay P (1981) Carbohydr Res 98:139–142CrossRefGoogle Scholar
  130. 130.
    Bonadies F, Di Fabio R, Bonini C (1984) J Org Chem 49:1647–1649CrossRefGoogle Scholar
  131. 131.
    Rauter AP, Canda T, Justino J, Ismael MI, Figueiredo JA (2004) J Carbohydr Chem 23:239–251CrossRefGoogle Scholar
  132. 132.
    Yadav JS, Subba Reddy BV, Suresh Reddy C (2004) Tetrahedron Lett 45:4583–4585CrossRefGoogle Scholar
  133. 133.
    Jarglis P, Lichtenthaler FW (1982) Tetrahedron Lett 23:3781–3784CrossRefGoogle Scholar
  134. 134.
    Lichtenthaler FW, Klingler FD, Jarglis P (1984) Carbohydr Res 132:C1–C4CrossRefGoogle Scholar
  135. 135.
    Lichtenthaler FW, Rönninger S, Jarglis P (1989) Liebigs Ann Chem 1153–1161Google Scholar
  136. 136.
    Lichtenthaler FW, Werner B (1999) Carbohydr Res 319:47–54CrossRefGoogle Scholar
  137. 137.
    Chmielewski M, Jurczak J, Maciejewski S (1987) Carbohydr Res 165:111–115CrossRefGoogle Scholar
  138. 138.
    Hamann H-J, Höft E, Mostowicz D, Mishnev A, Urbañczyk-Lipkowska Z, Chmielewski M (1997) Tetrahedron 53:185–192CrossRefGoogle Scholar
  139. 139.
    Mostowicz D, Jurczak M, Hamann H-J, Höft E, Chmielewski M (1998) Eur J Org Chem 2617–2621Google Scholar
  140. 140.
    Panfil I, Mostowicz D, Chmielewski M (1999) Pol J Chem 73:1099–1110Google Scholar
  141. 141.
    Socha D, Jurczak M, Chmielewski M (1997) Tetrahedron 53:739–746CrossRefGoogle Scholar
  142. 142.
    Rabiczko J, Chmielewski M (1999) J Org Chem 64:1347–1351CrossRefGoogle Scholar
  143. 143.
    Panfil I, Urbañczyk-Lipkowska Z, Suwiñka K, Solecka J, Chmielewski M (2002) Tetrahedron 58:1199–1212CrossRefGoogle Scholar
  144. 144.
    Panfil I, Solecka J, Chmielewski M (2006) J Carbohydr Chem 25:673–684CrossRefGoogle Scholar
  145. 145.
    Paniczek K, Jurczak M, Solecka J, Urbaczyk-Lipkowska Z, Chmielewski M (2007) J Carbohydr Chem 26:195–211CrossRefGoogle Scholar
  146. 146.
    Stecko S, Frelek J, Chmielewski M (2009) Tetrahedron Asymmetry 20:1778–179CrossRefGoogle Scholar
  147. 147.
    Ferrieres V, Bertho JN, Plusquellec D (1998) Carbohydr Res 311:25–35CrossRefGoogle Scholar
  148. 148.
    Roussel M, Moutard S, Perly B, Lefeuvre M, Benvegnu T, Plusquellec D (2003) Carbohydr Res 338:375–378CrossRefGoogle Scholar
  149. 149.
    Salam MA, Isbell HS (1982) Carbohydr Res 101:255–261CrossRefGoogle Scholar
  150. 150.
    Bertho J-N, Coué A, Ewing DF, Goodby JW, Letellier P, Mackenzie G, Plusquellec D (1997) Carbohydr Res 300:341–346CrossRefGoogle Scholar
  151. 151.
    Berchel M, Lemiegre L, Trepouth S, Lambert O, Jeftic J, Benvegnu T (2008) Tetrahedron Lett 49:7419–7422CrossRefGoogle Scholar
  152. 152.
    Berchel M, Lemiegre L, Jeftic J, Benvegnu T (2008) Tetrahedron Lett 49:4690–4692CrossRefGoogle Scholar
  153. 153.
    Guilbot J, Benvegnu T, Legros N, Plusquellec D, Dedieu JC, Gulik A (2001) Langmuir 17:613–618CrossRefGoogle Scholar
  154. 154.
    Gaertzen O, Misske AM, Wolbers P, Hoffmann HMR (1999) Synlett 1041–1044Google Scholar
  155. 155.
    Gaertzen O, Misske AM, Wolbers P, Hoffmann HMR (1999) Tetrahedron Lett 40:6359–6363CrossRefGoogle Scholar
  156. 156.
    Polakova M, Pitt N, Tosin M, Murphy PV (2004) Angew Chem Int Ed 43:2518–2521CrossRefGoogle Scholar
  157. 157.
    Polakova M, Pitt N, Tosin M, Murphy PV (2007) Chem Eur J 13:902–909CrossRefGoogle Scholar
  158. 158.
    Rat S, Mathiron D, Michaud P, Kovensky J, Wadouachi A (2007) Tetrahedron 63:12424–12428CrossRefGoogle Scholar
  159. 159.
    Doyle D, Murphy PV (2008) Carbohydr Res 343:2535–2544CrossRefGoogle Scholar
  160. 160.
    Rauter AP, Weidmann H (1982) Liebigs Ann Chem 2231–2237Google Scholar
  161. 161.
    Pudelko M, Lindgren A, Tengel T, Reis CA, Elofsson M (2006) Kihlberg. J Org Biomol Chem 4:713–720CrossRefGoogle Scholar
  162. 162.
    Angata T, Varki A (2002) Chem Rev 102:439–469CrossRefGoogle Scholar
  163. 163.
    Pan GG, Melton LD (2006) Carbohydr Res 341:730–737CrossRefGoogle Scholar
  164. 164.
    Colombo R, Anastasia M, Rota P, Allevi P (2008) Chem Commun 5517–5519Google Scholar
  165. 165.
    Buali T, Bratosin D, Pons A, Montreuil J, Zanetta JP (2003) FEBS Lett 534:185–189CrossRefGoogle Scholar
  166. 166.
    Bratosin D, Pauli A, Moicean AD, Zanetta JP, Montreuil J (2007) Biochimie 89:355–359CrossRefGoogle Scholar
  167. 167.
    Gervay J, Ramamoorthy PS, Mamuya NN (1997) Tetrahedron 53:11039–11048CrossRefGoogle Scholar
  168. 168.
    Andersson L, Kenne L (2000) Carbohydr Res 329:257–268CrossRefGoogle Scholar
  169. 169.
    Andersson L, Kenne L (2003) Carbohydr Res 338:85–93CrossRefGoogle Scholar
  170. 170.
    Defossemont GM, Mincher DJ (2003) Carbohydr Res 338:563–565CrossRefGoogle Scholar
  171. 171.
    Yuan N, Kitagawa Y, Fukudome M, Fujita K (2007) Org Lett 9:4591–4594CrossRefGoogle Scholar
  172. 172.
    Queneau Y, Jarosz S, Lewandowski B, Fitremann J (2007) Adv Carbohydr Chem Biochem 61:217–292CrossRefGoogle Scholar
  173. 173.
    Queneau Y, Fitremann J, Trombotto S (2004) C R Chimie 7:177–188CrossRefGoogle Scholar
  174. 174.
    Brochette-Lemoine S, Joannard D, Descotes G, Bouchu A, Queneau Y (1999) J Mol Catal A Chem 150:31–36CrossRefGoogle Scholar
  175. 175.
    Lemoine S, Thomazeau C, Joannard D, Trombotto S, Descotes G, Bouchu A, Queneau Y (2000) Carbohydr Res 326:176–184CrossRefGoogle Scholar
  176. 176.
    Trombotto S, Violet-Courtens E, Cottier L, Queneau Y (2004) Top Catal 27:31–37CrossRefGoogle Scholar
  177. 177.
    Weidenhagen R, Lorenz S (1957) Angew Chem 69:641–641CrossRefGoogle Scholar
  178. 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 57–94Google Scholar
  179. 179.
    Lichtenthaler FW, Peters S (2004) C R Chimie 7:65–90CrossRefGoogle Scholar
  180. 180.
    Lichtenthaler FW (1998) Carbohydr Res 313:69–89CrossRefGoogle Scholar
  181. 181.
    Lichtenthaler FW (2002) Acc Chem Res 35:728–737CrossRefGoogle Scholar
  182. 182.
    Lichtenthaler FW, Klimesch R, Muller V, Kunz M (1993) Liebigs Ann Chem 975–980Google Scholar
  183. 183.
    Trombotto S, Bouchu A, Descotes G, Queneau Y (2000) Tetrahedron Lett 41:8273–8277CrossRefGoogle Scholar
  184. 184.
    Trombotto S, Danel M, Fitremann J, Bouchu A, Queneau Y (2003) J Org Chem 68:6672–6678CrossRefGoogle Scholar
  185. 185.
    Pierre R, Chambert S, Alirachedi F, Danel M, Trombotto S, Doutheau A, Queneau Y (2008) C R Chimie 11:61–66CrossRefGoogle Scholar
  186. 186.
    Listkowski A, Ing P, Cheaib R, Chambert S, Doutheau A, Queneau Y (2007) Tetrahedron:Asymmetry 18:220–2210CrossRefGoogle Scholar
  187. 187.
    Cheaib R, Listkowski A, Chambert S, Doutheau A, Queneau Y (2008) Tetrahedron Asymmetry 19:1919–1933CrossRefGoogle Scholar
  188. 188.
    Dean B, Oguchi H, Cai S, Otsuji E, Tashiro K, Hakomori S, Toyokuni T (1993) Carbohydr Res 245:175–192CrossRefGoogle Scholar
  189. 189.
    Shiozaki M, Shimozato R, Watanabe Y, Mochizuki T (2006) JP 2006008539, Chem Abs 144:101029Google Scholar
  190. 190.
    Schmidt RR (1996) In: Kahn SH, O’Neill RA (eds) Modern methods in carbohydrate synthesis. Harwood Academic, Amsterdam, pp 20–54Google Scholar
  191. 191.
    Schmidt RR (1986) Angew Chem 25:213–236CrossRefGoogle Scholar
  192. 192.
    Klotz W, Schmidt RR (1993) Liebigs Ann Chem 683–690Google Scholar
  193. 193.
    Le Chevalier A, Pierre R, Kanso R, Chambert S, Doutheau A, Queneau Y (2006) Tetrahedron Lett 47:2431–2434CrossRefGoogle Scholar
  194. 194.
    Sol V, Charmot A, Krausz P, Trombotto S, Queneau Y (2006) J Carbohydr Chem 25:345–360CrossRefGoogle Scholar
  195. 195.
    Ménard F, Sol V, Ringot C, Granet R, Alves S, Le Morvan C, Queneau Y, Ono N, Krausz P (2009) Bioorg Med Chem 17:7647–7657CrossRefGoogle Scholar
  196. 196.
    Chambert S, Doutheau A, Queneau Y, Cowling SJ, Goodby JW, Mackenzie G (2007) J Carbohydr Chem 26:27–39CrossRefGoogle Scholar
  197. 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 8:142–150CrossRefGoogle Scholar
  198. 198.
    Queneau Y, Gagnaire J, West JJ, Mackenzie G, Goodby JW (2001) J Mater Chem 11:2839–2844CrossRefGoogle Scholar
  199. 199.
    Molinier VP, Kouwer HJ, Queneau Y, Fitremann J, Mackenzie G, Goodby JW (2003) Chem Commun 2860–2861Google Scholar
  200. 200.
    Kouwer MVP, JJ FJ, Bouchu A, Mackenzie G, Queneau Y, Goodby JW (2006) Chem Eur J 12:3547–3557CrossRefGoogle Scholar
  201. 201.
    Molinier V, Kouwer PJJ, Fitremann J, Bouchu A, Mackenzie G, Queneau Y, Goodby JW (2007) Chem Eur J 13:1763–1775CrossRefGoogle Scholar
  202. 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 36:1971–2032CrossRefGoogle Scholar
  203. 203.
    Molinier V, Fenet B, Fitremann J, Bouchu A, Queneau Y (2005) J Colloid Interface Sci 286:360–368CrossRefGoogle Scholar
  204. 204.
    Queneau Y, Chambert S, Besset C, Cheaib R (2008) Carbohydr Res 343:1999–2009CrossRefGoogle Scholar
  205. 205.
    Ali Rachedi F, Chambert S, Ferkous F, Queneau Y, Cowling SJ, Goodby JW (2009) Chem Commun 6355–6357Google Scholar
  206. 206.
    Xavier NM, Chambert S, Rauter AP, Queneau Y unpublishedGoogle Scholar
  207. 207.
    Araújo AC, Nicotra F, Costa B, Giagnoni G, Cipolla L (2008) Carbohydr Res 343:1840–1848CrossRefGoogle Scholar
  208. 208.
    Velazquez S, Jimeno ML, Huss S, Balzarini J, Camarasa M-J (1994) J Org Chem 59:7661–7670CrossRefGoogle Scholar
  209. 209.
    Gregori A, Alibés R, Bourdelande JL, Font J (1998) Tetrahedron Lett 39:6963–6966CrossRefGoogle Scholar
  210. 210.
    Alibés R, Bourdelande JL, Gregori A, Font J, Rustullet A, Parella T (2003) J Carbohydr Chem 22:501–511CrossRefGoogle Scholar
  211. 211.
    Yu M, Lynch V, Pagenkopf BL (2001) Org Lett 3:2563–2566CrossRefGoogle Scholar
  212. 212.
    Rauter A, Ferreira M, Duarte T, Piedade F, Silva M, Santos H (2000) Carbohydr Res 325:1–15CrossRefGoogle Scholar
  213. 213.
    Rauter AP, Oliveira O, Canda T, Leroi E, Ferreira H, Ferreira MJ, Ascenso JA (2002) J Carbohydr Chem 21:257–274CrossRefGoogle Scholar
  214. 214.
    Yu M, Pagenkopf BL (2003) Tetrahedron 59:2765–2771CrossRefGoogle Scholar
  215. 215.
    Haveli SD, Sridhar PR, Suguna P, Chandrasekaran S (2007) Org Lett 9:1331–1334CrossRefGoogle Scholar
  216. 216.
    Yin J, Linker T (2009) Chem Eur J 15:49–52CrossRefGoogle Scholar
  217. 217.
    Yin J, Sommermann T, Linker T (2007) Chem Eur J 13:10152–10167CrossRefGoogle Scholar
  218. 218.
    de Oliveira RB, Alves RJ, de Souza JD, Prado MAF (2003) J Braz Chem Soc 14:442–448CrossRefGoogle Scholar
  219. 219.
    Rungeler P, Castro V, Mora G, Goren N, Vichnewski W, Pahl HL, Merfort I, Schmidt TJ (1999) Bioorg Med Chem 7:2343–2352CrossRefGoogle Scholar
  220. 220.
    Oh S, Jeong IH, Shin W-S, Wang Q, Lee S (2006) Bioorg Med Chem Lett 16:1656–1659CrossRefGoogle Scholar
  221. 221.
    Li D-H, Zhu T-J, Liu H-B, Fang Y-C, Gu Q-Q, Zhu W-M (2006) Arch Pharm Res 29:624–626CrossRefGoogle Scholar
  222. 222.
    Cateni F, Zilic J, Zacchigna M, Bonivento P, Frausin F, Scarcia V (2006) Eur J Med Chem 41:192–200CrossRefGoogle Scholar
  223. 223.
    Prasad KR, Gholap SL (2008) J Org Chem 73:2–11CrossRefGoogle Scholar
  224. 224.
    Mereyala HB, Joe M (2001) Curr Med Chem AntiCancer Agents 1:293–300CrossRefGoogle Scholar
  225. 225.
    Gesson J-P, Jacquesy JC, Mondon M (1989) Tetrahedron 45:2627–2640CrossRefGoogle Scholar
  226. 226.
    Bennet M, Gill GB, Pattenden G, Shuker AJ, Stapleton A (1991) J Chem Soc Perkin Trans 1:929–937Google Scholar
  227. 227.
    Rychlik M, Schieberle P (1998) J Agric Food Chem 46:5163–5169CrossRefGoogle Scholar
  228. 228.
    Liu H-M, Zhang F, Zhang J, Shi L (2003) Carbohydr Res 338:1737–1743CrossRefGoogle Scholar
  229. 229.
    Xavier NM, Rauter AP (2007) Org Lett 9:3339–3341CrossRefGoogle Scholar
  230. 230.
    Xavier NM, Silva S, Madeira PJA, Florêncio MH, Silva FVM, Justino J, Thiem J, Rauter AP (2008) Eur J Org Chem 2008:6134–6143CrossRefGoogle Scholar
  231. 231.
    Xavier NM, Madeira PJA, Florêncio MH, Rauter AP (2009) Eur J Org Chem 2009:4983–4991CrossRefGoogle Scholar
  232. 232.
    Zhang J, Clive DLJ (1999) J Org Chem 64:770–779CrossRefGoogle Scholar

Copyright information

© Springer 2010

Authors and Affiliations

  • Nuno M. Xavier
    • 1
    • 2
    • 3
    • 4
  • Amélia P. Rauter
    • 1
  • Yves Queneau
    • 2
    • 3
    • 4
    Email author
  1. 1.Centro de Química e Bioquímica, Departamento de Química e BioquímicaFaculdade de Ciências da Universidade de LisboaLisboaPortugal
  2. 2.Laboratoire de Chimie OrganiqueINSA LyonVilleurbanneFrance
  3. 3.Institut de Chimie et Biochimie Moléculaires et SupramoléculairesUMR 5246, Université Lyon 1, Bâtiment CPEVilleurbanneFrance
  4. 4.Université de Lyon, INSA-Lyon, CNRS, CPE-LyonVilleurbanneFrance

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