O-Glycosylations under neutral or basic conditions

Journal of the Chemical Society. Perkin Transactions 1

Volumn 2, Issue 20, 2002, Pages 2219-2233

  Jensen, Knud J ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CHEMICAL ACTIVATION; CHEMICAL MODIFICATION; PHENOLS;

ALIPHATIC GLYCOSIDES; ARYL GLYCOSIDES; GLYCOSYL DONORS; GLYCOSYLATIONS; LEWIS ACID; OLIGOSACCHARIDE;

CHEMICAL REACTIONS;

EID: 0036026456     PISSN: 14727781     EISSN: 13645463     Source Type: Journal    
DOI: 10.1039/b110071h     Document Type: Review

References (123)

1. A. Michael Am. Chem. J. 1879, 1, 305.
2. E. Fischer Chem. Ber. 1893, 26, 2400.
3. E. Fischer Chem. Ber. 1895, 28, 1145.
4. E. Fischer, L. Beesch Chem. Ber. 1894, 27, 2478.
5. E. Fischer, L. Beesch Chem. Ber. 1896, 29, 2927.
6. W. Koenigs, E. Knorr Chem. Ber. 1901, 34, 957.
7. H. Paulsen Angew. Chem., Int. Ed. Engl. 1982, 21, 155.
8. H. Paulsen, in Modern Methods in Carbohydrate Synthesis, ed. S. H. Khan and R. A. O’Neill, Harword Academic Publishers, Amsterdam, 1996, pp. 1–19.
9. R.R. Schmidt, J.C. Castro-Palomino, O. Retz Pure Appl. Chem. 1999, 71, 729-744.
10. K.J. Jensen, K. Bock, M. Meldal J. Chem. Soc., Perkin Trans. 1 1993, 2119.
11. J. Banoub, P. Boullanger, D. Lafont Chem. Rev. 1992, 92, 1167.
12. K. Toshima, K. Tatsuta Chem. Rev. 1993, 93, 1503.
13. P. Collins, R. Ferrier, Monosaccharides, Wiley, Chichester, 1995.
14. G.-J. Boons Tetrahedron 1996, 52, 1095.
15. B.G. Davis J. Chem. Soc., Perkin Trans. 1 2000, 2137.
16. J. Conchie, G.A. Levvy, C.A. Marsh Adv. Carbohydr. Chem. 1957, 12, 157.
17. R.U. Lemieux, K.B. Hendricks, R.V. Sticks, K. James J. Am. Chem. Soc. 1975, 97, 4056.
18. L.G. Green and S.V. Ley, in Carbohydrates in Chemistry and Biology, eds. B. Ernst, G. W. Hart and P. Sinaÿ, vol. 1, 2000, pp. 427–448.
19. T. Nukada, A. Bérces, D.M. Whitfield Carbohydr. Res. 2002, 337, 765.
20. H. Paulsen, W.P. Trautwein, F.G. Espinosa, K. Heyns Chem. Ber. 1967, 100, 2822.
21. H. Paulsen, C.P. Herold Chem. Ber. 1970, 103, 2450.
22. T. Nukada, A. Bérces, M.Z. Zgierski, D.M. Whitfield J. Am. Chem. Soc. 2001, 123, 13291.
23. A. Bérces, G. Enright, T. Nukada, D.M. Whitfield J. Am. Chem. Soc. 1998, 120, 5460.
24. J. March, Advanced Organic Chemistry, 3rd edn., Wiley, New York, 1985.
25. E. Fischer, E.F. Armstrong Chem. Ber. 1901, 34, 2885.
26. E. Fischer, K. Raske Chem. Ber. 1909, 42, 1465.
27. F. Mauthner J. Prak. Chem. 1910, 82, 271.
28. F. Mauthner J. Prak. Chem. 1911, 83, 556.
29. F. Mauthner J. Prak. Chem. 1912, 85, 564.
30. F. Mauthner J. Prak. Chem. 1915, 91, 174.
31. E. Glaser, W. Wulwek Biochem. Z. 1924, 145, 514.
32. E. Glaser, A.C. Thaler Arch. Pharm. (Weinheim, Ger.) 1926, 264, 228.
33. T. Osawa, Y. Nakazawa Biochim. Biophys. Acta 1966, 130, 56.
34. F. Ballardie, B. Capon, J.D.G. Sutherland, D. Cocker, M. Sinnott J. Chem. Soc., Perkin Trans. 1 1973, 2418.
35. E. Zissis, C.P.J. Glaudemans Carbohydr. Res. 1976, 50, 292.
36. K. Takeo, K. Mine, T. Kuge Carbohydr. Res. 1976, 48, 197.
37. L.H. George, Jr., E.L. May, E. Mosettig J. Org. Chem. 1950, 15, 884-889.
38. M. Seidman, K.P. Link J. Am. Chem. Soc. 1950, 72, 4324.
39. I.C.M. Dea Carbohydr. Res. 1969, 11, 363-367.
40. F.L. Weitl, M. Sovak, M. Ohno J. Med. Chem. 1976, 19, 353.
41. E.T. Jones, A. Robertson J. Chem. Soc. 1930, 1699.
42. R.R. Schmidt, J. Michel Angew. Chem. 1980, 92, 763.
43. L.A. Carpino, H. Ringsdorf, H. Ritter Makromol. Chem. 1976, 177, 1631.
44. C.K. De Bruyne, F. Van Wijnendaele Carbohydr. Res. 1967, 4, 102.
45. T. Osawa, Y. Nakazawa Biochim. Biophys. Acta 1966, 130, 56.
46. C.K. De Bruyne, H. Versele, M. Clayessens Nature 1965, 900.
47. Y.V. Voznyi, I.S. Kalicheva, A.A. Galoyan Bioorg. Khim. 1982, 8, 1388.
48. Y.V. Voznyi, I.S. Kalicheva, A.A. Galoyan Bioorg. Khim. 1985, 11, 970.
49. T. Iversen, R. Johansson Synthesis 1979, 823.
50. S.A. Abbas, K.L. Matta Carbohydr. Res. 1983, 124, 115.
51. C. Hansson, E. Rosengren Acta Chem. Scand. 1976, 30, 871.
52. K. Brewster, J.M. Harrison, T.D. Inch Tetrahedron Lett. 1979, 52, 5051.
53. H.P. Kleine, D.V. Weinberg, R.J. Kaufman, R.S. Sidhu Carbohydr. Res. 1985, 142, 333.
54. A. Lubineau, E. Meyer, P. Place Carbohydr. Res. 1992, 228, 191.
55. D. Loganathan, G.K. Trivedi Carbohydr. Res. 1987, 162, 117.
56. S. Halazy, V. Berges, A. Ehrhard, C. Danzin Bioorg. Chem. 1990, 18, 330.
57. P. Maillard, J.-L. Guerquin-Kern, C. Huel, M. Momenteau J. Org. Chem. 1993, 58, 2774.
58. S. Mabic, C. Benezra, J.-P. Lepoittevin Tetrahedron Lett. 1993, 34, 4531.
59. A. Lubineau, E. Meyer, P. Place Carbohydr. Res. 1992, 228, II-84 191-204.
60. R. Roy, F. Tropper, A. Romanowska, M. Letellier, L. Cousineau, S.J. Meunier, J. Boratynski Glycoconjugate Journal 1991, 8, 75.
61. R. Roy, F.O. Andersson, G. Harms, S. Kelm, R. Schauer Angew. Chem. 1992, 31, 1478.
62. R. Roy, F.D. Tropper, A. Ramanowska Bioconj. Chem. 1992, 3, 256.
63. R. Begbie Carbohydr. Res. 1969, 10, 311-312.
64. M.G. Vafina, N.V. Molodtsov Carbohydr. Res. 1974, 32, 161.
65. F.M. Delmotte, J.-P. D. J. Privat, M.L.P. Monsigny Carbohydr. Res. 1975, 40, 353.
66. M.G. Vafina, N.V. Molodtsov, L.I. Fedoreeva Carbohydr. Res. 1975, 44, 142.
67. K.L. Matta, J.J. Barlow Carbohydr. Res. 1976, 48, 65.
68. M.-C. Courtin-Duchateau, A. Veyriéres Carbohydr. Res. 1978, 65, 23.
69. G.Y. Wiederschain, I.K. Kozlova, G.S. Ilyina, M.A. Mikhaylova, E.M. Beyer Carbohydr. Res. 1992, 224, 255.
70. E. Vis, H.G. Fletcher J. Am. Chem. Soc. 1957, 79, 1182.
71. J. Gervay, S. Danishefsky J. Org. Chem. 1991, 56, 5448.
72. R.G. Dushin, S.J. Danishefsky J. Am. Chem. Soc. 1992, 114, 3471.
73. R.G. Dushin, S.J. Danishefsky J. Am. Chem. Soc. 1992, 114, 655.
74. E. Fischer, L. von Mechel Chem. Ber. 1916, 49, 2813.
75. G. Zemplen, A. Müller Chem. Ber. 1929, 62, 2107.
76. A. Müller Chem. Ber. 1929, 62, 2793.
77. R.R. Schmidt Angew. Chem. 1986, 98, 213.
78. H.J. Koeners, A.J. de Kok, C. Romers, J.H. van Boom Recl. Trav. Chim. Pays-Bas 1980, 99, 355.
79. S.K. Sharma, G. Corrales, S. Penadés Tetrahedron Lett. 1995, 36, 5627.
80. T. Mukaiyama, Y. Hashimoto, Y. Hayashi, S. Shoda Chem. Lett. 1984, 557.
81. U. Huchel, C. Schmidt, R.R. Schmidt Tetrahedron Lett. 1995, 36, 9457.
82. U. Huchel, C. Schmidt, R.R. Schmidt Eur. J. Org. Chem. 1998, 1353.
83. K. Briner, A. Vasella Helv. Chim. Acta 1989, 72, 1371.
84. A. Vasella Pure Appl. Chem. 1991, 63, 507.
85. E. Bozó, A. Vasella Helv. Chim. Acta 1994, 77, 745.
86. R. Jeanloz, H.G. Fletcher, C.S. Hudson J. Am. Chem. Soc. 1948, 70, 4055.
87. R.K. Ness, H.G. Fletcher, C.S. Hudson J. Am. Chem. Soc. 1950, 72, 2200.
88. J.M. Fréchet, C. Schuerch J. Am. Chem. Soc. 1972, 94, 604.
89. J.M. Fréchet, C. Schuerch Carbohydr. Res. 1972, 22, 399-412.
90. R.U. Lemieux, J.I. Hayni Can. J. Chem. 1965, 43, 2162.
91. N.M. Malkar, J.L. Lauer-Fields, G.B. Fields Tetrahedron Lett. 2000, 41, 1137.
92. E. Fischer, H. Fischer Chem. Ber. 1910, 43, 2535.
93. J. Gervay, in Organic Synthesis: Theory and Applications, 1998, vol. 4, pp. 121–153.
94. D.R. Mootoo, P. Konradsson, U. Udodong, B. Fraser-Reid J. Am. Chem. Soc. 1988, 110, 5583.
95. B. Helferich, R. Gootz Chem. Ber. 1929, 62, 2791.
96. J. Thiem, B. Meyer Chem. Ber. 1980, 113, 3075.
97. J. Gervay, T.N. Nguyen, M.J. Hadd Carbohydr. Res. 1997, 300, 119.
98. B. Ernst, T. Winkler Tetrahedron Lett. 1989, 30, 3081.
99. M.J. Hadd, J. Gervay Carbohydr. Res. 1999, 320, 61.
100. S.N. Lam, J. Gervay-Hague Org. Lett. 2002, 4, 2039.
101. J. Gervay, M.J. Hadd J. Org. Chem. 1997, 62, 6961.
102. W.J. Serfontein, J.H. Jordaan, J. White Tetrahedron Lett. 1964, 18, 1069.
103. R.U. Lemieux, T.L. Nagabushan, S.W. Gunner Can. J. Chem. 1968, 46, 405.
104. Z. Smiatacz, E. Paszkiewicz Bull. Pol. Acad. Sci., Chem. 1986, 34, 381.
105. Y. Pocker, G.T. Spyridis J. Am. Chem. Soc. 2002, 124, 7390.
106. G. Springer, C. Elam, A. Edwards, C. Bowe, D. Boyles, J. Bartmess, M. Chandler, K. West, J. Williams, J. Green, R.M. Pagni, G.W. Kabalka J. Org. Chem. 1999, 64, 2202.
107. G. Böhm, H. Waldmann Liebigs Ann. 1996, 613-619.
108. H. Schene, H. Waldmann Eur. J. Org. Chem. 1998, 1227.
109. H. Schene, H. Waldmann Chem. Commun. 1998, 2759.
110. H. Schene, H. Waldmann Synthesis 1999, 1411.
111. G. Böhm, H. Waldmann Liebigs Ann. 1996, 612.
112. U. Schmid, H. Waldmann Chem. Eur. J. 1998, 4, 494.
113. A. Lubineau, B. Drouillat J. Carbohydr. Chem. 1997, 16, 1179.
114. L. Petersen, K.J. Jensen J. Org. Chem. 2001, 66, 6268.
115. W. Hengstenberg, K. Wallenfels Carbohydr. Res. 1969, 11, 85.
116. B. Capon Tetrahedron Lett 1963, 14, 9111.
117. B. Capon, M.C. Smith, E. Anderson, R.H. Dahm, G.H.J. Sankey Chem. Soc. (B) 1969, 1038.
118. S. Koto, N. Morishima, Y. Miyata, S. Zen Bull. Chem. Soc. Jpn. 1976, 49, 2639.
119. S. Oscarson, F.W. Sehgelmeble J. Am. Chem. Soc. 2000, 122, 8869.
120. L. Petersen, K.J. Jensen J. Chem. Soc., Perkin Trans. 1 2001, 2175.
121. R. Caputo, H. Kunz, D. Mastroianni, G. Palumbo, S. Pedatella, F. Solla Eur. J. Org. Chem. 1999, 11, 3147.
122. J.F. Tolborg, K.J. Jensen Chem. Commun. 2000, 147-148.
123. J.B. Laursen, L. Petersen, K.J. Jensen Org. Lett. 2001, 3, 687.