Glycosyl fluoride: A superb glycosyl donor in glycosylation

Proceedings of the Japan Academy Series B: Physical and Biological Sciences

Volumn 78, Issue 4, 2002, Pages 73-83

  Mukaiyama, Teruaki ^a   Jona, Hideki ^a,b  

^a KITASATO INSTITUTE   (Japan)

^b BANYU PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Catalytic and stereoselective glycosylation; F1 antigen; Glycosyl fluorides; One pot glycosylation; Protic acids; Silver tetrakis(pentafluorophenyl)borate; Stannic chloride; Stannous chloride; Trityl tetrakis(pentafluorophenyl)borate

Indexed keywords

EID: 0036553873     PISSN: 03862208     EISSN: 03862208     Source Type: Journal    
DOI: 10.2183/pjab.78.73     Document Type: Review

References (134)

1. Koenigs, W., and Knorr, E. (1901) Ber. Dtsch. Chem. Ges. 34, 957-981.
2. Paulsen, H. (1982) Angew. Chem., Int. Ed. Engl. 21, 155-224;
3. Schmidt, R. R. (1986) Angew. Chem., Int. Ed. Engl. 25, 212-235;
4. Kunz, H. (1987) Angew. Chem., Int. Ed. Engl. 26, 294-308;
5. Sinaÿ, P. (1991) Pure Appl. Chem. 63, 519-528;
6. Suzuki, K., and Nagasawa, T. (1992) J. Synth. Org. Chem. Jpn. 50, 378-390;
7. Toshima, K., and Tatsuta, K. (1993) Chem. Rev. 93, 1503-1531;
8. Ernst, B., Hart, G. W., and Sinaÿ, P. (2000) Carbohydrate in Chemistry and Biology, part 1, Wiley-VCH, Weinheim.
9. Mukaiyama, T., Murai, Y., and Shoda, S. (1981) Chem. Lett. 1981, 431-432.
10. Kerr, J. A. (1991) CRC Hand Book of Chemistry and Physics, 72nd ed., CRC Press, Boca Raton, pp. 9(105)-9(113).
11. Shimizu, M., Togo, H., and Yokoyama, M. (1998) Synthesis 1998, 799-822;
12. Yokoyama, M. (2000) Carbohydr. Res. 327, 5-14;
13. Toshima, K. (2000) Carbohydr. Res. 327, 15-26.
14. Brauns, D. H. (1923) J. Am. Chem. Soc. 45, 833-835.
15. Mukaiyama, T., Hashimoto, Y., and Shoda, S. (1983) Chem. Lett. 1983, 935-938.
16. Rosenbrook, W. Jr., Riley, D. A., and Lartey, P. A. (1985) Tetrahedron Lett. 26, 3-4;
17. Posner, G. H., and Haines, S. R. (1985) Tetrahedron Lett. 26, 5-8.
18. Nicolaou, K. C., Ladduwahetty, T., Randal, J. L., and Chucholowski, A. (1986) J. Am. Chem. Soc. 108, 2466-2467.
19. Cumpstey, I., Fairbanks, A. J., and Redgrave, A. J. (2001) Org. Lett. 3, 2371-2374.
20. Hayashi, M., Hashimoto, S., and Noyori, R. (1984) Chem. Lett. 1984, 1747-1750;
21. Szarek, W. A., Grynkiewicz, G., Doboszewski, B., and Hay, G. W. (1984) Chem. Lett. 1984, 1751-1754.
22. Bröder, W., and Kunz, H. (1990) Synlett 1990, 251-252;
23. Bröder, W., and Kunz, H. (1993) Carbohydr. Res. 249, 221-241.
24. Palme, M., and Vasella, A. (1995) Helv. Chim. Acta 78, 959-969.
25. Miethchen, R., Hager, C., and Hein, M. (1997) Synthesis 1997, 159-161.
26. Kunz, H., and Sanger, W. (1985) Helv. Chim. Acta 68, 283-287.
27. Burkart, M. D., Zhang, Z., Hung, S.-C., and Wong, C.-H. (1997) J. Am. Chem. Soc. 119, 11743-11746.
28. Lal, G. S., Pez, G. P., Pesaresi, R. J., Prozonic, F. M., and Cheng, H. (1999) J. Org. Chem. 64, 7048-7054.
29. Ernst, B., and Winkler, T. (1989) Tetrahedron Lett. 30, 3081-3084.
30. Miethchen, R., Gabriel, T., and Kolp, G. (1991) Synthesis 1991, 885-888;
31. Miethchen, R., and Rentsch, D. (1994) Synthesis 1994, 827-831;
32. Miethchen, R., and Gabriel, T. (1993) Chem. Ber. 126, 2309-2316;
33. Miethchen, R., and Gabriel, T. (1994) J. Fluorine Chem. 67, 11-15.
34. Kondo, T., Tomoo, T., Abe, H., Isobe, M., and Goto, T. (1996) Chem. Lett. 1996, 337-338;
35. Teichmann, M., Descotes, G., and Lafont, D. (1993) Synthesis 1993, 889-894;
36. Lichtenthaler, F. W., Kläres, U., Lergenmüller, M., and Schwidetzky, S. (1992) Synthesis 1992, 179-184.
37. Goggin, K. D., Lambert, J. F., and Walinsky, S. W. (1994) Synlett 1994, 162-164.
38. Miethchen, R., and Kolp, G. (1993) J. Fluorine Chem. 60, 49-55.
39. Nicolaou, K. C., Dolle, R. E., Papahatjis, D. P., and Randall, J. L. (1984) J. Am. Chem. Soc. 106, 4189-4192.
40. Horne, G., and Mackie, W. (1999) Tetrahedron Lett. 40, 8697-8700.
41. Caddick, S., Motherwell, W. B., and Wilkinson, J. A. (1991) J. Chem. Soc., Chem. Commun. 1991, 674-675;
42. Caddick, S., Gazzard, L., Motherwell, W. B., and Wilkinson, J. A. (1996) Tetrahedron 52, 149-156.
43. Gordon, D. M., and Danishefsky, S. J. (1990) Carbohydr. Res. 206, 361-366.
44. Shimizu, M., Nakahara, Y., and Yoshioka, H. (1999) J. Fluorine Chem. 97, 57-60.
45. Ogawa, T., and Takahashi, Y. (1985) Carbohydr. Res. 138, C5-C9;
46. Takahashi, Y., and Ogawa, T. (1987) Carbohydr. Res. 164, 277-296.
47. Hashimoto, S., Hayashi, M., and Noyori, R. (1984) Tetrahedron Lett. 25, 1379-1382.
48. Nicolaou, K. C., Chucholowski, A., Dolle, R. E., and Randall, J. L. (1984) J. Chem. Soc., Chem. Commun. 1984, 1155-1156;
49. Kunz, H., and Waldmann, H. (1985) J. Chem. Soc., Chem. Commun. 1985, 638-640;
50. Kunz, H., and Sager, W. (1985) Helv. Chim. Acta 68, 283-287;
51. Yamaguchi, M., Horiguchi, A., Fukuda, A., and Minami, T. (1990) J. Chem. Soc., Chem. Commun. 1990, 1079-1082.
52. Kreuzer, M., and Thiem, J. (1986) Carbohydr. Res. 149, 347-361;
53. Jünnemann, J., Lundt, I., and Thiem, J. (1991) Liebigs Ann. Chem. 1991, 759-764.
54. Matsumoto, T., Maeta, H., Suzuki, K., and Tsuchihashi, G. (1988) Tetrahedron Lett. 29, 3567-3570, 3571-3574, 3575-3578;
55. Suzuki, K., Maeta, H., and Matsumoto, T. (1989) Tetrahedron Lett. 30, 4853-4856;
56. Suzuki, K., and Matsumoto, T. (1993) J. Synth. Org. Chem. Jpn. 51, 718-732.
57. Suzuki, K., Maeta, H., Suzuki, T., and Matsumoto, T. (1989) Tetrahedron Lett. 30, 6879-6882.
58. Nicolaou, K. C., Caulfield, T. J., Kataoka, H., and Stylianides, N. A. (1990) J. Am. Chem. Soc. 112, 3693-3695;
59. Nicolaou, K. C., Hummel, C. W., and Iwabuchi, Y. (1992) J. Am. Chem. Soc. 114, 3126-3128;
60. Matsuzaki, Y., Ito, Y., Nakahara, Y., and Ogawa, T. (1993) Tetrahedron Lett. 34, 1061-1064.
61. Maeta, H., Matsumoto, T., and Suzuki, K. (1993) Carbohydr. Res. 249, 49-56.
62. Kobayashi, S., Koide, K., and Ohno, M. (1990) Tetrahedron Lett. 31, 2435-2438.
63. Wessel, H. P. (1990) Tetrahedron Lett. 31, 6863-6866;
64. Wessel, H. P., and Ruiz, N. (1991) J. Carbohydr. Chem. 10, 901-910.
65. Böhm, G., and Waldmann, H. (1995) Tetrahedron Lett. 36, 3843-3846;
66. Böhm, G., and Waldmann, H. (1990) Liebigs Ann. Chem. 1996, 613-619;
67. Böhm, G., and Waldmann, H. (1996) Liebigs Ann. Chem. 1996, 621-625.
68. Hosono, S., Kim, W.-S., Sasai, H., and Shibasaki, M. (1995) J. Org. Chem. 60, 4-5.
69. Kim, W.-S., Hosono, S., Sasai, H., and Shibasaki, M. (1995) Tetrahedron Lett., 36, 4443-4446.
70. Kim, W.-S., Sasai, H., and Shibasaki, M. (1996) Tetrahedron Lett. 37, 7797-7800.
71. Yu, L., Chen, D., Li, J., and Wang, P. G. (1997) J. Org. Chem. 62, 3575-3581.
72. Toshima, K., Kasumi, K., and Matsumura, S. (1998) Synlett 1998, 643-645;
73. Toshima, K., Kasumi, K., and Matsumura, S. (1999) Synlett 1999, 813-815.
74. Takeuchi, K., and Mukaiyama, T. (1998) Chem. Lett. 1998, 555-556.
75. Mukaiyama, T., Takeuchi, K., Jona, H., Maeshima, H., and Saitoh, T. (2000) Helv. Chim. Acta 83, 1901-1918.
76. Mukaiyama, T., Jona, H., and Takeuchi, K. (2000) Chem. Lett. 2000, 696-697;
77. Jona, H., Takeuchi, K., and Mukaiyama, T. (2000) Chem. Lett. 2000, 1278-1279.
78. Jona, H., Mandai, H., and Mukaiyama, T. (2001) Chem. Lett. 2001, 426-427;
79. Jona, H., Mandai, H., Chavasiri, W., Takeuchi, K., and Mukaiyama, T. (2002) Bull. Chem. Soc. Jpn. 75, 291-309;
80. Mukaiyama, T., Suenaga, M., Chiba, H., and Jona, H. (2002) Chem. Lett. 2002, 56-57.
81. Yanagisawa, M., and Mukaiyama, T. (2001) Chem. Lett. 2001, 224-225.
82. Mukaiyama, T., Maeshima, H., and Jona, H. (2001) Chem. Lett. 2001, 388-389.
83. Jona, H., Maeshima, H., and Mukaiyama, T. (2001) Chem. Lett. 2001, 726-727.
84. Packard, G. K., and Rychnovsky, S. D. (2001) Org. Lett. 3, 3393-3396.
85. Mukaiyama, T., Kobayashi, S., and Shoda, S. (1984) Chem. Lett. 1984, 907-910.
86. Chien, J. C. W., Tsai, W.-.M., and Rausch, M. D. (1991) J. Am. Chem. Soc. 113, 8570-8571.
87. Uchiro, H., and Mukaiyama, T. (1996) Chem. Lett. 1996, 79-80;
88. Takeuchi, K., Higuchi, S., and Mukaiyama, T. (1997) Chem. Lett. 1997, 969-970.
89. Mukaiyama, T., Miyazaki, K., and Uchiro, H. (1998) Chem. Lett. 1998, 635-636.
90. Uchiro, H., and Mukaiyama, T. (1997) Chem. Lett. 1997, 121-122;
91. Takeuchi, K., Tamura, T., and Mukaiyama, T. (2000) Chem. Lett. 2000, 124-125.
92. Mootoo, D. R., Konradsson, P., Udodong, U., and Fraser-Reid, B. (1998) J. Am. Chem. Soc. 110, 5583-5584.
93. Barrena, M. I., Echarri, R., and Castillón, S. (1996) Synlett 1990, 675-676;
94. Green, L., Hinzen, B., Ince, S. J., Langer, P., Ley, S. V., and Warriner, S. L. (1998) Synlett 1998, 440-442;
95. Baeschlin, D. K., Green, L. G., Hahn, M. G., Hinzen, B., Ince, S. J., and Ley, S. V. (2000) Tetrahedron: Asymmetry 11, 173-197.
96. Mukaiyama, T., Yanagisawa, M., Iida, D., and Hachiya, I. (2000) Chem. Lett. 2000, 606-607;
97. Yanagisawa, M., Shimamura, T., Iida, D. Matsuo, J., and Mukaiyama, T. (2000) Chem. Pharm. Bull. 48, 1838-1840.
98. Banoub, J. (1992) Chem. Rev. 92, 1167-1195.
99. Mukaiyama, T., Katsurada, M., and Takashima, T. (1991) Chem. Lett. 1991, 985-988;
100. Fukase, K., Kinoshita, I., Kanoh, T., Nakai, Y., Hasuoka, A., and Kusumoto, S. (1996) Tetrahedron 52, 3897-3904.
101. Pearson, R. G. (1963) J. Am. Chem. Soc. 85, 3533-3539;
102. Akiba, K., and Inamoto, N. (1975) J. Synth. Org. Chem. Jpn. 33, 834-841.
103. Mukaiyama, T., Ikegai, K., Jona, H., Hashihayata, T., and Takeuchi, K. (2001) Chem. Lett. 2001, 840-841.
104. Mukaiyama, T., Ikegai, K., Hashihayata, T., Kiyota, K., and Jona, H. (to be published in Chem. Lett.).
105. Kanie, O., Ito, Y., and Ogawa, T. (1994) J. Am. Chem. Soc. 116, 12073-12074.
106. Veeneman, G. H. (1999) In Carbohydrate Chemistry (ed. Boons, G.-J.). Blackie Academic & Professional Press, London, pp. 98-174.
107. Ono, Y., and Yashima, T. (eds.) (2000) Science and Technology of Zeorite. Koudansya Press, Tokyo, pp. 119-163 (in Japanese "Zeoraito no Kagaku to Kougaku").
108. Editorial Committees of Zeorite and its Application (ed.) (1967) Zeorite and its Application. Gihoudou Press, Tokyo, pp. 170-193 (in Japanese "Zeoraito to so no Riyou").
109. Kevill, D. N., and Sutthoff, R. F. (1977) J. Chem. Soc., Perkin Trans. 2. 1977, 201-200;
110. Kato, T., Tanaka, M., Hoshikawa, M., and Yagi, M. (1998) Tetrahedron Lett. 39, 7553-7556.
111. Raghavan, S., and Kahne, D. (1993) J. Am. Chem. Soc. 115, 1580-1581;
112. Yamada, H., Harada, T., and Takahashi, T. (1994) J. Am. Chem. Soc. 116, 7919-7920;
113. Yamada, H., Harada, T., Miyazaki, H., and Takahashi, T. (1994) Tetrahedron Lett. 35, 3979-3982;
114. Chenault, H. K., and Castro, A. (1994) Tetrahedron Lett. 35, 9145-9148;
115. Boons, G.-J., and Zhu, T. (1997) Synlett 1997, 809-811;
116. Green, L., Hinzen, B., Ince, S. J., Langer, P., Ley, S. V., and Warriner, S. L. (1998) Synlett 1998, 440-442;
117. Yu, B., Yu, H., Hui, Y., and Han, X. (1999) Tetrahedron Lett. 40, 8591-8594;
118. Zhang, Z., Ollmann, I. R., Ye, X.-S., Wischnat, R., Baasov, T., and Wong, C.-H. (1999) J. Am. Chem. Soc. 121, 734-753;
119. Yu, B., Xie, J., Deng, S., and Hui, Y. (1999) J. Am. Chem. Soc. 121, 12196-12197;
120. Takeuchi, K., Tamura, T., and Mukaiyama, T. (2000) Chem. Lett. 2000, 124-125;
121. Takahashi, T., Adachi, M., Matsuda, A., and Doi, T. (2000) Tetrahedron Lett. 41, 2599-2603;
122. Ye, X.-S., and Wong, C.-H. (2000) J. Org. Chem. 65, 2410-2431;
123. Burkhart, F., Zhang, Z., Wacowich-Sgarbi, S., and Wong, C.-H. (2001) Angew. Chem., Int. Ed. Engl. 40, 1274-1277;
124. Yamada, H., Takimoto, H., Ikeda, T., Tsukamoto, K., Harada, T., and Takahashi, T. (2001) Synlett 2001, 1751-1754.
125. Konradsson, P., Mootoo, D. R., McDevitt, R. E., and Fraser-Reid, B. (1990) J. Chem. Soc., Chem. Commun. 1990, 270-272;
126. Veeneman, G. H., van Leeuwen, S. H., and van Boom, J. H. (1990) Tetrahedron Lett. 31, 1331-1334.
127. Yamashita, Y., Chung, Y. S., Sawada, T., Horie, R., Saito, T., Murayama, K., Kannagi, R., and Sowa, M. (1998) Oncology 55, 70-76;
128. Yamashita, Y., Chung, Y. S., Horie, R., Kannagi, R., and Sowa, M. (1995) J. Natl. Cancer Inst. 87, 441-446;
129. Yamashita, Y., Cluing, Y. S., Sawada, T., Kondo, Y., Hirayama, K., Inui, A., Nakata, B., Okuno, M., Horie, R., Saito, T., Murayama, K., Kannagi, R., and Sowa, M. (1994) Int. J. Cancer 58, 349-355.
130. Qiu, D., and Koganty, R. R. (1997) Tetrahedron Lett. 38, 45-48;
131. Chen, X.-T., Sames, D., and Danishefsky, S. J. (1998) J. Am. Chem. Soc. 120, 7760-7769.
132. Sharp, J. K., McNeil, M., and Albersheim, P. (1984) J. Biol. Chem. 259, 11321-11337;
133. Verduyn, R., Douwes, M., van der Klein, P. A. M., Mösinger, E. M., van der Marel, G. A., and van Boom, J. H. (1993) Tetrahedron 49, 7301-7316;
134. Yamada, H., Takimoto, H., Ikeda, T., Tsukamoto, K., Harada, T., and Takahashi, T. (2001) Synlett 2001, 1751-1754.