Simplifying oligosaccharide synthesis: Boronate diesters as cleavable protecting groups

Synlett

Volumn , Issue 5, 1998, Pages 487-488

  Cross, G G ^a   Whitfield, D M ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001031172     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1706     Document Type: Article

References (32)

1. a) R. Liang, L. Yan, J. Loebach, M. Ge, Y. Uozumi, K. Sekanina, N. Horan, J. Gildersleeve, C. Thompson, A. Smith, K. Biswas, W.C. Still, D. Kahne, Science, 274, 1520 (1996).
2. b) J.A. Hunt, W.R. Roush, J. Am. Chem. Soc., 118, 9998 (1996).
3. c) J. Rademann, R.R. Schmidt, Tetrahedron Lett., 37, 3989 (1996).
4. d) L. Yan, C.M. Taylor, R. Goodnow Jr., D. Kahne, J. Am. Chem. Soc., 116, 6953 (1994).
5. e) G.C. Look, Y. Ichikawa, G.J. Shen, P.W. Cheng, C.H. Wong, J. Org. Chem., 58, 4326 (1993).
6. f) S. Köpper, Carbohydr. Res., 265, 161 (1994).
7. g) R.L. Halcomb, H. Huang, C.H. Wong, J. Am. Chem. Soc., 116, 11315 (1994).
8. h) S.J. Danishefsky, K.F. McClure, J.T. Randolph, R.B. Ruggeri, Science, 260, 1307 (1993).
9. i) K.C. Nicolau, N. Winssinger, J. Pastor, F. DeRoose, J. Am. Chem. Soc., 119, 449 (1997).
10. j) R. Rodebaugh, S. Joshi, B. Fraser-Reid, H.M. Geysen, J. Org. Chem., 62, 5660 (1997).
11. S.P. Douglas, D.M. Whitfield, J.J. Krepinsky, J. Am. Chem. Soc., 113, 5095 (1991).
12. S.P. Douglas, D.M. Whitfield, J.J. Krepinsky, J. Am. Chem. Soc., 117, 2116 (1995).
13. For other applications of PEG to carbohydrates see a) Y. Ito, T. Ogawa, J. Am. Chem. Soc., 119, 5562 (1997).
14. b) L.O. Kononov, Y. Ito, T. Ogawa, Tetrahedron Lett., 38, 1599 (1997).
15. c) A.A. Kandil, N. Chan, M. Klein, P. Chong, Glycoconjugate J., 14, 13 (1997).
16. d) C.M. Dreef-Tromp, H.A.M. Willems, P. Westerduin, P. van Veelen, C.A.A. van Boeckel, Bioorganic Med. Chem. Lett., 7, 1175 (1997).
17. e) L. Jiang, R.C. Hartley, T.H. Chan, Chem. Commun., 2193 (1996).
18. f) Z.G. Wang, S.P. Douglas, J.J. Krepinsky, Tetrahedron Lett., 39, 6985 (1996).
19. g) Y. Ito, O. Kanie, T. Ogawa, Ang. Chem. Int. Ed. Engl., 35, 2510 (1996).
20. For different uses of boronates with carbohydrates sec a) S. Langston, B. Bernet, A. Vasella, Helv. Chim. Acta, 77, 2341 (1994).
21. b) W. V. Dahloff, R. Köster, Heterocycles, 18, 421 (1982).
22. P.M. Åberg, L. Blomberg, H. Lönn, T. Norberg, J. Carbohydr. Chem., 13, 141 (1994).
23. R.J. Ferrier, Adv. Carbohydr. Chem. Biochem., 35, 31 (1978).
24. R.J. Ferrier, A.J. Hannaford, W.G. Overend, B.C. Smith, Carbohydr. Res., 1, 38 (1965).
25. G.H. Veeneman, S.H. van Leeuwen, J.H. van Boom, Tetrahedron Lett., 31, 1331 (1990).
26. -1 was typically used.
27. S.P. Douglas, D.M. Whitfield, J.J. Krepinsky, J. Carbohydr. Chem., 12, 131 (1993).
28. O.T. Leung, S.P. Douglas, H.Y.S. Pang, D.M. Whitfield, J.J. Krepinsky, New J. Chem., 18, 349 (1994).
29. O. Kanie, S.C. Crawley, M.M. Palcic, O. Hindsgaul, Carbohydr. Res., 243, 139 (1993).
30. S. Mehta, D.M. Whitfield submitted.
31. D.M. Whitfield, C.J. Ruzicka, J.P. Carver, J.J. Krepinsky, Can. J. Chem., 65, 693 (1987).
32. R.U. Lemieux, Can. J. Chem., 29, 1079 (1951).