Skip to main content

Phase transfer catalysis in carbohydrate chemistry

  • Chapter
Handbook of Phase Transfer Catalysis

Abstract

Although there have been many books and reviews about phase transfer catalysis (PTC) in organic chemistry, except for one Russian paper this chapter constitutes the first survey of its kind for carbohydrate chemistry. As a consequence, this survey has tried to be as exhaustive as space limitation afforded. This chapter presents a critical analysis of the widespread applications of PTC to carbohydrate syntheses. In order to be somewhat systematic, this chapter is divided into three main sections. The first concerns non anomeric transformations and the second deals with anomeric glycosylations. An intermediate section describes the above two transformations in the context of nucleosides. The last section illustrates the reversed applications in which carbohydrate derivatives are now acting themselves as phase transfer catalysts.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Haines, A.H. (1976) Adv. Carbohydr. Chem. Biochem.,33, 11.

    CAS  Google Scholar 

  2. Dehmlow, E.V. and Dehmlow, S.S. (1983) Phase Transfer Catalysis, 2nd edn, Verlag Chemie, Weinheim.

    Google Scholar 

  3. Nouguier, R. (1982) Tetrahedron Lett., 23, 3505.

    CAS  Google Scholar 

  4. Di Cesare, P. and Gross, B. (1996) Carbohydr. Res., 48, 271.

    Google Scholar 

  5. Rosenthal, A.F., Vargas, L.A. and Dixon, J.F. (1977) Chem. Phys. Lipids, 20, 205.

    CAS  Google Scholar 

  6. Zhdanov, Yu.A., Alekseev, Yu.E., Doroshenko, S.S. et al. (1978) Dokl. Akad. Nauk SSSR, 238, 1102.

    CAS  Google Scholar 

  7. Zhdanov, Yu.A., Alekseev, Yu.E., Korol, E.L. et al. (1993) Zh. Obshch. Khim., 63, 1174; Chem. Abstr., 1994,120, 192093y.

    CAS  Google Scholar 

  8. Szeja, W. (1990) Pol. J. Chem., 54, 1301.

    Google Scholar 

  9. Nouguier, R. and Medani, C. (1987) Tetrahedron Lett., 28, 319.

    CAS  Google Scholar 

  10. Nouguier, R.M. and Mchich, M. (1985) J. Org. Chem., 50, 3296.

    CAS  Google Scholar 

  11. Szeja, W., Kokt, I. and Grynkiewicz, G. (1989) Reel. Trav. Chim. Pays-Bas, 108, 224.

    CAS  Google Scholar 

  12. Dubreuil, D., Cleophax, J. and Loupy, A. (1994) Carbohydr. Res., 252, 149.

    CAS  Google Scholar 

  13. Garegg, P.J., Iversen, T. and Oscarson, S. (1976) Carbohydr. Res., 50, C12.

    CAS  Google Scholar 

  14. Garegg, P.J., Iversen, T. and Oscarson, S. (1977) Carbohydr. Res., 53, C5.

    CAS  Google Scholar 

  15. Garegg, P.J. (1984) Pure Appl. Chem., 56, 845.

    CAS  Google Scholar 

  16. Garegg, P.J., Kvarnstrom, I., Niklasson, A. etal. (1993) Carbohydr. Chem., 12, 933.

    CAS  Google Scholar 

  17. Szeja, W. (1981) J. Chem. Soc., Chem. Commun., 215.

    Google Scholar 

  18. Verez Bencomo, V., Saenz, G.A. de la C., Garcia Fernandez, G. et al. (1981) Rev. Cubana Farm., 15, 169.

    CAS  Google Scholar 

  19. Verez Bencomo, V., Diaz Rodriguez, P., Garcia Fernandez, G. and Basterrachea Rey, M.C.M. (1981) Rev. Cubana Farm., 15, 26.

    CAS  Google Scholar 

  20. Pozsgay, V. (1979) Carbohydr. Res., 69, 284.

    CAS  Google Scholar 

  21. Szeja, W. (1979) Synthesis, 821.

    Google Scholar 

  22. Box, V.G.S., Box, L.L. and Roberts, E.V.E. (1983) Carbohydr. Res., 119, 273.

    CAS  Google Scholar 

  23. Szeja, W. (1983) Carbohydr. Res., 115, 240.

    CAS  Google Scholar 

  24. Gizaw, Y. and BeMiller, J.N. (1995) Carbohydr. Res., 266, 81.

    CAS  Google Scholar 

  25. Mallet. A., Mallet, J.-M. and Sinay, P. (1994) Tetrahedron: Asymmetry, 5, 2593.

    CAS  Google Scholar 

  26. Szeja, W. (1980) Pol. J. Chem., 54, 1323.

    CAS  Google Scholar 

  27. Garegg, P.J., Iversen, T., Johnsson, R. and Lindberg, B. (1984) Carbohydr. Res., 130, 322.

    CAS  Google Scholar 

  28. Brånalt, J., Kvarnstrom, I., Niklasson, G. et al. (1994) J. Org. Chem., 59, 1783.

    Google Scholar 

  29. Szeja, W. (1985) Synthesis, 983.

    Google Scholar 

  30. Szeja, W. (1986) Carbohydr. Res., 158,245.

    CAS  Google Scholar 

  31. Szeja, W. (1988) Carbohydr. Res., 183, 135.

    CAS  Google Scholar 

  32. Becker, B. and Thiem, J. (1994) Tetrahedron: Asymmetry, 5, 2339.

    CAS  Google Scholar 

  33. Di Cesare, P. and Gross, B. (1979) Synthesis, 458.

    Google Scholar 

  34. Zhdanov, Yu,A. and Alekseev, Yu.E. (1986) Zh. Vses. Khim. O-va. im D.I. Mendeleeva, 31, 188; Chem. Abstr., 105, 134244c.

    CAS  Google Scholar 

  35. Rathjens, A., Thiem, J. and Schwengers, D. (1995) 8th European Carbohydrate Symposium, Seville, Spain, July 2–7, 1995, Abstr. A133.

    Google Scholar 

  36. Zhdanov, Yu.A., Alekseev, Yu.E., Korol, E.L. and Sudareva, T.P. (1992) Dokl. Akad. Nauk SSSR, 322, 902.

    CAS  Google Scholar 

  37. Zhdanov, Yu.A., Alekseev, Yu.E., Sudareva, T.P. and Samarskova, N.N. (1993) Zh. Obsch. Khim., 63, 914; Chem. Abstr., 1994,120, 77561n.

    CAS  Google Scholar 

  38. Zhdanov, Yu.A., Polenov, V.A., Alekseeva, V.G. et al. (1983) Dokl. Akad Nauk SSSR, 283, 402; Chem. Abstr., 1986,105,43162h.

    Google Scholar 

  39. Di Cesare, P. and Gross, B. (1980) Synthesis, 714.

    Google Scholar 

  40. Neumann, K. (1992) Acta Chem. Scand, 46, 913.

    CAS  Google Scholar 

  41. Zhdanov, Yu.A., Alekseev, Yu.E., Palui, I.N. and Serebrennikova, E.V. (1985) Dokl. Akad. Nauk SSSR, 268, 883.

    Google Scholar 

  42. Kim, K.S. and Szarek, W.A. (1978) Synthesis, 48.

    Google Scholar 

  43. Norman, D.G., Reese, C.B. and Serafinowska, H.T. (1988) Synthesis, 15.

    Google Scholar 

  44. Vega-Perez, J.M., Espartero, J.L. and Alcudia, F. (1993) J. Carbohydr. Chem., 12, 477.

    CAS  Google Scholar 

  45. Morris, P.E. and Kiely, D.E. (1982) Org. Chem., 52, 1149.

    Google Scholar 

  46. Morris, P.E., Kiely, D.E., Vigee, G.S. and Kovac, P. (1990) J. Carbohydr. Chem., 9, 661.

    CAS  Google Scholar 

  47. Sele, A., Baehler, B. and Tronchet, J.M.J. (1979) Helv. Chim. Acta, 62, 866.

    CAS  Google Scholar 

  48. Zhdanov, Yu.A., Alekseev, Yu.E. and Doroshenko, S.S. (1982) Dokl. Akad. Nauk SSSR, 262, 1147.

    CAS  Google Scholar 

  49. Bessodes, M. and Antonakis, K. (1985) Tetrahedron Lett., 26, 1305.č

    CAS  Google Scholar 

  50. Roy, R. and Laferriere, C.A. (1990) Can. J. Chem.,6S, 2045.

    Google Scholar 

  51. Sakakibara, T. and Sudoh, R. (1975) J. Org. Chem., 40, 2823.

    CAS  Google Scholar 

  52. Sakakibara, T., Yamada, M. and Sudoh, R. (1976) J. Org. Chem., 41, 736.

    CAS  Google Scholar 

  53. Zhdanov, Yu.A., Polenov, V.A., Korol, E.L. et al. (1982) Dokl. Akad Nauk SSSR, 262, 887.

    CAS  Google Scholar 

  54. Zhdanov, Yu.A. and Uzlova, L.A. (1983) Zh. Obsch. Khim., 53, 484; Chem. Abstr., 99, 22777e.

    CAS  Google Scholar 

  55. Valpuesta Fernández, M., Durante-Lanes, P. and López-Herrera, F.J. (1990) Tetrahedron, 46,7911.

    Google Scholar 

  56. Duchaussoy, P., Di Cesare, P. and Gross, B. (1979) Synthesis, 198.

    Google Scholar 

  57. Pino-González, M.S., López-Herrera, F.J., Sarabia-Garcia, F. et al. (1995) 8th European Carbohydrate Symposium, Seville, Spain, July 2–7, 1995, Abstr. A98, A99.

    Google Scholar 

  58. Hansson, C. and Rosengren, E. (1976) Acta Chem. Scand., Ser. B, 30, 871.

    Google Scholar 

  59. Brewster, K., Harrison, J.M. and Inch, T.D. (1979) Tetrahedron Lett., 5051.

    Google Scholar 

  60. Dess, D., Kleine, H.P., Weinberg, D.V. et al. (1981) Synthesis, 883.

    Google Scholar 

  61. Kleine, H.P., Weinberg, D.V., Kaufman, R.J. and Sidhu, R.S. (1985) Carbohydr. Res., 142, 333.

    CAS  Google Scholar 

  62. Iversen, T. and Johansson, R. (1979) Synthesis, 823.

    Google Scholar 

  63. Abbas, S.A., Barlow, J.J. and Matta, K.L. (1982) Carbohydr. Res., 100, C33.

    CAS  Google Scholar 

  64. Kleine, H.P. and Sidhu, R.S. (1988) Carbohydr. Res., 182, 307.

    CAS  Google Scholar 

  65. Demetzos, C., Skaltsounis, A.-L., Tillequin, F. and Koch, M. (1990) Carbohydr. Res., 207, 131.

    CAS  Google Scholar 

  66. Roy, R. and Tropper, F. (1990) Synth. Commun., 20, 2097.

    CAS  Google Scholar 

  67. Roy, R., Tropper, F.D., Romanowska, A. et al. (1991) Glycoconj. J., 8, 75.

    CAS  Google Scholar 

  68. Roy, R. and Tropper, F.D. (1991) Can. J. Chem., 69, 817.

    CAS  Google Scholar 

  69. Roy, R., Tropper, F.D. and Romanowska, A. (1992) Bioconj. Chem., 3, 256.

    CAS  Google Scholar 

  70. Roy, R., Tropper, F.D., Morrison, T. and Boratynski, J. (1991) J. Chem. Soc., Chem. Commun., 536.

    Google Scholar 

  71. Toshima, K. and Tatsuta, K. (1993) Chem. Rev., 93, 1503.

    CAS  Google Scholar 

  72. Tropper, F.D. (1992) PhD Dissertation, University of Ottawa.

    Google Scholar 

  73. Rothermel, J. and Faillard, H. (1990)Carbohydr. Res., 196, 29.

    CAS  Google Scholar 

  74. Reinhard, B. and Faillard, H. (1994) Liebigs Ann. Chem., 193.

    Google Scholar 

  75. Di Cesare, P. and Gross, B. (1977) Carbohydr. Res., 58, C1.

    Google Scholar 

  76. Szeja, W. (1988) Synthesis, 223.

    Google Scholar 

  77. Knöchel, A., Rudolph, G. and Thiem, J. (1974) Tetrahedron Lett., 551.

    Google Scholar 

  78. Rothermel, J. and Faillard, H. (1989) Biol. Chem. Hoppe-Seyler, 370, 1077.

    CAS  Google Scholar 

  79. Tropper, F.D., Andersson, F.O., Grand-Maître, C. and Roy, R. (1991) Synthesis, 734.

    Google Scholar 

  80. Tropper, F.D., Andersson, F.O., Grand-Maitre, C. and Roy, R. (1992) Carbohydr. Res., 229,149.

    CAS  Google Scholar 

  81. Cao, S., Meunier, S.J., Andersson, F.O. et al. (1994) Tetrahedron: Asymmetry, 5, 2303.

    CAS  Google Scholar 

  82. Bogusiak, J. and Szeja, W. (1985) Pol. J. Chem., 59, 293.

    CAS  Google Scholar 

  83. Chrétien, F., Di Cesare, P. and Gross, B. (1988) J. Chem. Soc., Perkin Trans. 1, 3297.

    Google Scholar 

  84. Roy, R., Zanini, D., Meunier, S.J. and Romanowska, A. (1994) ACS Symp. Ser., 560,104.

    CAS  Google Scholar 

  85. Roy, R., Zanini, D., Meunier, S.J. and Romanowska, A. (1995) J. Chem. Soc., Chem. Commun., 1869.

    Google Scholar 

  86. Park, W.K.C., Meunier, S.J., Zanini, D. and Roy, R. (1995) Carbohydr. Lett., 1,179.

    CAS  Google Scholar 

  87. Tropper, F.D., Andersson, F.O., Cao, S. and Roy, R. (1992) J. Carbohydr. Chem., 11, 741.

    CAS  Google Scholar 

  88. Szeja, W. and Bogusiak, J. (1988) Synthesis, 224.

    Google Scholar 

  89. Hamacher, K. (1984) Carbohydr. Res., 128, 291.

    CAS  Google Scholar 

  90. Bogusiak, J. and Szeja, W. (1985) Carbohydr. Res., 141,165.

    CAS  Google Scholar 

  91. Roy, R. and Kim, J.M., unpublished results.

    Google Scholar 

  92. Roy, R. and Cao, S., unpublished results.

    Google Scholar 

  93. Roy, R., Tropper, F.D. and Grand-Maitre, C (1991) Can. J. Chem., 69, 1462.

    CAS  Google Scholar 

  94. Cao, S., Tropper, F.D. and Roy, R. (11995) Tetrahedron, 51, 6679.

    Google Scholar 

  95. Roy, R. (1995) In Modern Methods in Carbohydrate Synthesis (eds S.W. Khan and R. O’Neil), Harwood Academic, Amsterdam, pp. 378–402.

    Google Scholar 

  96. Kunz, H. and Waldmann, H. (1985) Angew. Chem., Int. Ed. Engl.,24, 883.

    Google Scholar 

  97. Tropper, F.D., Andersson, F.O., Braun, S. and Roy, R. (1992) Synthesis, 618.

    Google Scholar 

  98. Rothermel, J., Weber, B. and Faillard, H. (1992) Liebigs Ann. Chem.,199.

    Google Scholar 

  99. Rothermel, J. and Faillard, H. (1990) Carbohydr. Res., 208, 251.

    CAS  Google Scholar 

  100. Winkeler, H.-D. and Seela, F. (1983) J. Org. Chem.,48, 3119.

    CAS  Google Scholar 

  101. Seela, F. and Steker, H. (1984) Tetrahedron Lett., 25, 5017.

    CAS  Google Scholar 

  102. Sekine, M. (1989) J. Org. Chem., 54,2321.

    CAS  Google Scholar 

  103. Rosemeyer, H., Kaiser, K. and Seela, F. (1985) J. Org. Chem., 50, 1847.

    CAS  Google Scholar 

  104. Seela, F. and Bourgeois, W. (1987) Heterocycles, 26, 1755.

    CAS  Google Scholar 

  105. Seela, F. and Driller, H. (1984) Liebigs Ann. Chem., 722.

    Google Scholar 

  106. Seela, F., Driller, H. and Liman, U. (1985) Liebigs Ann. Chem., 312.

    Google Scholar 

  107. Seela, F. and Hasselman, D. (1980) Chem. Ber., 113, 3389.

    CAS  Google Scholar 

  108. Seela, F., Hasselmann, D. and Winkeler, H.-D. (1982) Liebigs Ann. Chem., 499.

    Google Scholar 

  109. Seela, F. and Kehne, A. (1983) Liebigs Ann. Chem.,876.

    Google Scholar 

  110. Seela, F. and Menknoff, S. (1985) Liebigs Ann. Chem., 1360.

    Google Scholar 

  111. Seela, F., Menknoff, S. and Behrendt, S. (1986) J. Chem. Soc., Perkin Trans. 2, 525.

    Google Scholar 

  112. Seela, F., Rosemeyer, H. and Bourgeois, W. (1987) Nucleic Acids Symp. Ser., 49.

    Google Scholar 

  113. Seela, F. and Steker, H. (1983) Liebigs Ann. Chem., 1576.

    Google Scholar 

  114. Seela, F. and Steker, H. (1985) Helv. Chim. Acta., 68, 563.

    CAS  Google Scholar 

  115. Seela, F. and Steker, H. (1985) J. Chem. Soc., Perkin Trans. 1, 2573.

    Google Scholar 

  116. Seela, F. and Steker, H. (1986) Helv. Chim. Acta, 69, 1602.

    Google Scholar 

  117. Seela, F. and Steker, H. (1984) Liebigs Ann. Chem.,1719.

    Google Scholar 

  118. Seela, F., Tran-Thi, Q.-H and Winkeler, H.-D. (1981) Chem. Ber., 114, 1217.

    CAS  Google Scholar 

  119. Seela, F. and Winkeler, H.-D. (1982) J. Org. Chem., 41, 226.

    Google Scholar 

  120. Seela, F. and Winkeler, H.-D. (1981) Angew. Chem., Int. Ed Engl., 20, 97.

    Google Scholar 

  121. Seela, F. and Winkeler, H.-D. (1982) Liebigs Ann. Chem., 1634.

    Google Scholar 

  122. Winkeler, H.-D., and Seela, F. (1980) Chem. Ber., 113, 2069.

    CAS  Google Scholar 

  123. Winkeler, H.-D. and Seela, F. (1984) Liebigs Ann. Chem., 708.

    Google Scholar 

  124. Seela, F. and Bourgeois, W. (1988) Synthesis, 938; (1989) 912.

    Google Scholar 

  125. Seela, F., Westermann, B. and Bindig, U. (1980) J. Chem. Soc., Perkin Trans. 1, 697.

    Google Scholar 

  126. Seela, F., Muth, H.-P. and Bindig, U. (1988) Synthesis, 670.

    Google Scholar 

  127. Seela, F., Kaiser, K and Bindig, U. (1988) Helv. Chim. Acta, 72, 868.

    Google Scholar 

  128. Kazimierczuk, Z. and Seela, F. (1990) Helv. Chim. Acta, 73, 316.

    CAS  Google Scholar 

  129. Kazimierczuk, Z. and Seela, F. (1990) Liebigs Ann. Chem., 647.

    Google Scholar 

  130. Rosemeyer, H. and Seela, F. (1988) Helv. Chim. Acta, 71, 1573.

    CAS  Google Scholar 

  131. Seela, F., Soulimane, T., Mersmann, K. and Jiirgens, T. (1990) Helv. Chim. Acta, 73, 1879.

    CAS  Google Scholar 

  132. Seela, F., Kehne, A. and Winkeler, H.-D. (1983) Liebigs Ann. Chem., 137.

    Google Scholar 

  133. Seela, F. and Menknoff, S. (1982) Liebigs Ann. Chem., 1405.

    Google Scholar 

  134. Rosemeyer, H., Kaiser, K. and Seela, F. (1985) Helv. Chim. Acta, 68, 534.

    CAS  Google Scholar 

  135. Seela, F., Lupke, U. and Hasselmann, D. (1980) Chem. Ber., 113, 2808.

    CAS  Google Scholar 

  136. Seela, F. and Winkeler, H.-D. (1979) Angew. Chem., Int. Ed. Engl., 18, 536.

    Google Scholar 

  137. Goldberg, Y. (1992) Phase Transfer Catalysis. Selected Problems and Applications, Gordon and Breach, New York.

    Google Scholar 

  138. Grouiller, A., Essadiq, H., Najib, B and Moliere, P. (1987) Synthesis, 1121.

    Google Scholar 

  139. Bessodes, M., Shamsazar, J. and Antonakis, K. (1988) Synthesis, 560.

    Google Scholar 

  140. Kobayashi, Y., Kumadaki, I., Ohsava, A. and Murakami, S. (1976) J. Chem. Soc., Chem. Commun., 430.

    Google Scholar 

  141. Akela, A. and Sherrington, D.C. (1982) Eur. Polym. J., 18, 301.

    Google Scholar 

  142. Gruber, H. and Greber, G. (1981) Monatsh. Chem., 112, 1063.

    CAS  Google Scholar 

  143. Deratani, A., Lelievre, G., Maroldo, T. and Sebille, B. (1989) Carbohydr. Res., 192, 215.

    CAS  Google Scholar 

  144. Trifonov, A.Z. and Nikoforov, T.T. (1984), J. Mol Catal., 24, 15.

    CAS  Google Scholar 

  145. Tanaka, N., Tamaguchi, A., Araki, Y. and Araki, M. (1987) Chem. Lett.,715.

    Google Scholar 

  146. Ganeshpure, P.A. and Satish, S. (1988) J. Chem. Soc., Chem. Commun., 981.

    Google Scholar 

  147. Fornassier, R., Reniero, F., Scrimin, P. and Tonellato, U. (1985) J. Org. Chem., 50, 3209.

    Google Scholar 

  148. Fornassier, R., Lucchini, V., Scrimin, P. and Tonellato, U. (1986) J. Org. Chem., 51, 1769.

    Google Scholar 

  149. Chenevert, R. and Chamberland, D. (1985) Chem. Lett., 1117.

    Google Scholar 

  150. Zhdanov, Yu.A., Alekseev, Yu.E., Korol, E.L. et al. (1993) Zh. Obsck Khim., 63, 1495; Chem. Abstr., 1994,120, 322868t.

    CAS  Google Scholar 

  151. Komiyyama, M. and Hirai, H. (1980) Makromol. Chem. Rapid. Commun., 2, 117, 601, 661, 707,715, 733,757, 759.

    Google Scholar 

  152. Hirai, H. (1984) J. Inclus. Phenom.,2,455.

    CAS  Google Scholar 

  153. Zahalka, H.A. and Alper, H. (1986) Organometallics, 5,1909.

    CAS  Google Scholar 

  154. Lee, J.-T. and Alper, H. (1990) Org. Chem., 55, 1854.

    CAS  Google Scholar 

  155. Lee, J.-T. and Alper, H. (1990) Tetrahedron Lett., 31, 1941.

    CAS  Google Scholar 

  156. Alper, H. (1987) ACS Symp. Ser., 326, 8.

    CAS  Google Scholar 

  157. Zahalka, H.A., Januszkiewicz, K. and Alper, H. (1986) J. Mol. Catal., 35, 249.

    CAS  Google Scholar 

  158. Harada, A., Hu, Y. and Takahashi, S. (1986) Chem. Lett., 2083.

    Google Scholar 

  159. Banfi, S., Colonna, S. and Julia, S. (1983) Synth. Commun., 13, 1049.

    CAS  Google Scholar 

  160. Rasmussen, J.K., Heilmann, S.M., Krepski, L.R. and Smith H.K., II (1982) ACS Symp. Ser., 326, 116.

    Google Scholar 

  161. Kunieda, N., Taguchi, H., Shiode, S. and Kinoshita, M. (1982) Makromol. Chem. Rapid Commun., 3, 395.

    CAS  Google Scholar 

  162. Taguchi, H., Kunieda, N. and Kinoshita, M. (1982) Makromol Chem. Rapid Commun., 3, 495.

    CAS  Google Scholar 

  163. Taguchi, H., Kunieda, N. and Kinoshita, M. (1983) Makromol Chem. Rapid. Commun., 184, 925.

    CAS  Google Scholar 

  164. Kunieda, N., Shiode, S., Ryoshi, H. et al. (1984) Makromol Chem. Rapid. Commun., 5, 137.

    CAS  Google Scholar 

  165. Alston, D.R., Slawin, A.M.Z., Stoddart, J.F. and Williams, D.J. (1985) Angew. Chem., Int. Ed. Engl., 24, 786.

    Google Scholar 

  166. Shimizu, S., Sasaki, Y. and Hirai, C. (1990) Bull Chem. Soc. Jpn., 63, 176.

    CAS  Google Scholar 

  167. Barak, G. and Sasson, Y. (1988) Bull Soc. Chim. Fr., 584.

    Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1997 Chapman & Hall

About this chapter

Cite this chapter

Roy, R. (1997). Phase transfer catalysis in carbohydrate chemistry. In: Sasson, Y., Neumann, R. (eds) Handbook of Phase Transfer Catalysis. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-0023-3_7

Download citation

  • DOI: https://doi.org/10.1007/978-94-009-0023-3_7

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-0-7514-0258-2

  • Online ISBN: 978-94-009-0023-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics