Vinyl glycosides in oligosaccharide synthesis. 2. The use of allyl and vinyl glycosides in oligosaccharide synthesis

Journal of Organic Chemistry

Volumn 61, Issue 13, 1996, Pages 4262-4271

  Boons, Geert Jan ^a   Isles, Stephen ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGOSACCHARIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030018326     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960131b     Document Type: Article

References (41)

1. Varki, A. Glycobiology 1993, 397.
2. For recent examples of elegant strategies for oligosaccharide synthesis see: (a) Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6656. (b) Mehta, S.; Pinto, B. M. Tetrahedron Lett. 1991, 32, 4435. (c) Nicolaou, K. C.; Caulfield, T. J.; Croneberg, R. D. Pure Appl. Chem. 1991, 63, 555. (d) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580. (e) Mehta, S.; Pinto, B. M. J. Org. Chem. 1993, 58, 3269. (f) Sliedrecht, L. A. J. M.; Zegelaar-Jaarveld, K.; van der Marel, G. A.; van Boom, J. H. Synlett 1993, 335. (g) Yamada, H.; Harada, T.; Miyazaki, H.; Takahishi, T. Tetrahedron Lett. 1994, 35, 3979. (h) Kanie, O.; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 12073. (i) Schmidt, R. R. Tetrahedron Lett. 1994, 35, 7927.
3. For recent examples of elegant strategies for oligosaccharide synthesis see: (a) Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6656. (b) Mehta, S.; Pinto, B. M. Tetrahedron Lett. 1991, 32, 4435. (c) Nicolaou, K. C.; Caulfield, T. J.; Croneberg, R. D. Pure Appl. Chem. 1991, 63, 555. (d) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580. (e) Mehta, S.; Pinto, B. M. J. Org. Chem. 1993, 58, 3269. (f) Sliedrecht, L. A. J. M.; Zegelaar-Jaarveld, K.; van der Marel, G. A.; van Boom, J. H. Synlett 1993, 335. (g) Yamada, H.; Harada, T.; Miyazaki, H.; Takahishi, T. Tetrahedron Lett. 1994, 35, 3979. (h) Kanie, O.; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 12073. (i) Schmidt, R. R. Tetrahedron Lett. 1994, 35, 7927.
4. For recent examples of elegant strategies for oligosaccharide synthesis see: (a) Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6656. (b) Mehta, S.; Pinto, B. M. Tetrahedron Lett. 1991, 32, 4435. (c) Nicolaou, K. C.; Caulfield, T. J.; Croneberg, R. D. Pure Appl. Chem. 1991, 63, 555. (d) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580. (e) Mehta, S.; Pinto, B. M. J. Org. Chem. 1993, 58, 3269. (f) Sliedrecht, L. A. J. M.; Zegelaar-Jaarveld, K.; van der Marel, G. A.; van Boom, J. H. Synlett 1993, 335. (g) Yamada, H.; Harada, T.; Miyazaki, H.; Takahishi, T. Tetrahedron Lett. 1994, 35, 3979. (h) Kanie, O.; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 12073. (i) Schmidt, R. R. Tetrahedron Lett. 1994, 35, 7927.
5. For recent examples of elegant strategies for oligosaccharide synthesis see: (a) Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6656. (b) Mehta, S.; Pinto, B. M. Tetrahedron Lett. 1991, 32, 4435. (c) Nicolaou, K. C.; Caulfield, T. J.; Croneberg, R. D. Pure Appl. Chem. 1991, 63, 555. (d) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580. (e) Mehta, S.; Pinto, B. M. J. Org. Chem. 1993, 58, 3269. (f) Sliedrecht, L. A. J. M.; Zegelaar-Jaarveld, K.; van der Marel, G. A.; van Boom, J. H. Synlett 1993, 335. (g) Yamada, H.; Harada, T.; Miyazaki, H.; Takahishi, T. Tetrahedron Lett. 1994, 35, 3979. (h) Kanie, O.; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 12073. (i) Schmidt, R. R. Tetrahedron Lett. 1994, 35, 7927.
6. For recent examples of elegant strategies for oligosaccharide synthesis see: (a) Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6656. (b) Mehta, S.; Pinto, B. M. Tetrahedron Lett. 1991, 32, 4435. (c) Nicolaou, K. C.; Caulfield, T. J.; Croneberg, R. D. Pure Appl. Chem. 1991, 63, 555. (d) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580. (e) Mehta, S.; Pinto, B. M. J. Org. Chem. 1993, 58, 3269. (f) Sliedrecht, L. A. J. M.; Zegelaar-Jaarveld, K.; van der Marel, G. A.; van Boom, J. H. Synlett 1993, 335. (g) Yamada, H.; Harada, T.; Miyazaki, H.; Takahishi, T. Tetrahedron Lett. 1994, 35, 3979. (h) Kanie, O.; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 12073. (i) Schmidt, R. R. Tetrahedron Lett. 1994, 35, 7927.
7. For recent examples of elegant strategies for oligosaccharide synthesis see: (a) Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6656. (b) Mehta, S.; Pinto, B. M. Tetrahedron Lett. 1991, 32, 4435. (c) Nicolaou, K. C.; Caulfield, T. J.; Croneberg, R. D. Pure Appl. Chem. 1991, 63, 555. (d) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580. (e) Mehta, S.; Pinto, B. M. J. Org. Chem. 1993, 58, 3269. (f) Sliedrecht, L. A. J. M.; Zegelaar-Jaarveld, K.; van der Marel, G. A.; van Boom, J. H. Synlett 1993, 335. (g) Yamada, H.; Harada, T.; Miyazaki, H.; Takahishi, T. Tetrahedron Lett. 1994, 35, 3979. (h) Kanie, O.; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 12073. (i) Schmidt, R. R. Tetrahedron Lett. 1994, 35, 7927.
8. For recent examples of elegant strategies for oligosaccharide synthesis see: (a) Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6656. (b) Mehta, S.; Pinto, B. M. Tetrahedron Lett. 1991, 32, 4435. (c) Nicolaou, K. C.; Caulfield, T. J.; Croneberg, R. D. Pure Appl. Chem. 1991, 63, 555. (d) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580. (e) Mehta, S.; Pinto, B. M. J. Org. Chem. 1993, 58, 3269. (f) Sliedrecht, L. A. J. M.; Zegelaar-Jaarveld, K.; van der Marel, G. A.; van Boom, J. H. Synlett 1993, 335. (g) Yamada, H.; Harada, T.; Miyazaki, H.; Takahishi, T. Tetrahedron Lett. 1994, 35, 3979. (h) Kanie, O.; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 12073. (i) Schmidt, R. R. Tetrahedron Lett. 1994, 35, 7927.
9. For recent examples of elegant strategies for oligosaccharide synthesis see: (a) Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6656. (b) Mehta, S.; Pinto, B. M. Tetrahedron Lett. 1991, 32, 4435. (c) Nicolaou, K. C.; Caulfield, T. J.; Croneberg, R. D. Pure Appl. Chem. 1991, 63, 555. (d) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580. (e) Mehta, S.; Pinto, B. M. J. Org. Chem. 1993, 58, 3269. (f) Sliedrecht, L. A. J. M.; Zegelaar-Jaarveld, K.; van der Marel, G. A.; van Boom, J. H. Synlett 1993, 335. (g) Yamada, H.; Harada, T.; Miyazaki, H.; Takahishi, T. Tetrahedron Lett. 1994, 35, 3979. (h) Kanie, O.; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 12073. (i) Schmidt, R. R. Tetrahedron Lett. 1994, 35, 7927.
10. For recent examples of elegant strategies for oligosaccharide synthesis see: (a) Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6656. (b) Mehta, S.; Pinto, B. M. Tetrahedron Lett. 1991, 32, 4435. (c) Nicolaou, K. C.; Caulfield, T. J.; Croneberg, R. D. Pure Appl. Chem. 1991, 63, 555. (d) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580. (e) Mehta, S.; Pinto, B. M. J. Org. Chem. 1993, 58, 3269. (f) Sliedrecht, L. A. J. M.; Zegelaar-Jaarveld, K.; van der Marel, G. A.; van Boom, J. H. Synlett 1993, 335. (g) Yamada, H.; Harada, T.; Miyazaki, H.; Takahishi, T. Tetrahedron Lett. 1994, 35, 3979. (h) Kanie, O.; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 12073. (i) Schmidt, R. R. Tetrahedron Lett. 1994, 35, 7927.
11. (a) Veeneman, G. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 275.
12. (b) Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331.
13. Fraser Reid, B.; Udodong, U. E.; Wu, Z.; Ottoson, H.; Merritt, J. R.; Rao, S.; Roberts, C.; Madsen, R. Synlett 1992, 12, 927.
14. Recently, thioglycosides with novel reactivities have been reported: (a) Boons, G. J.; Grice, P.; Ley, S. V.; Yeung, L. L. Tetrahedron Lett. 1983, 34, 8523. (b) Boons, G. J.; Geurtsen, R.; Holmes, D. Tetrahedron Lett. 1995, 36, 6325.
15. Recently, thioglycosides with novel reactivities have been reported: (a) Boons, G. J.; Grice, P.; Ley, S. V.; Yeung, L. L. Tetrahedron Lett. 1983, 34, 8523. (b) Boons, G. J.; Geurtsen, R.; Holmes, D. Tetrahedron Lett. 1995, 36, 6325.
16. Roy, R.; Anderson, F. O.; Telellier, M. Tetrahedron Lett. 1992, 33, 6053.
17. Marra, A.; Esnault, J.; Veyrieres, A.; Sinaÿ, P. J. Am. Chem. Soc. 1992, 114, 6354.
18. Boons, G. J.; Isles, S. Tetrahedron Lett. 1994, 35, 3593.
19. Boons, G. J.; Burton, A.; Isles, S. J. Chem. Soc., Chem Commun. 1996, 141.
20. Corey, E. J.; Suggs, W. J. J. Org. Chem. 1973, 38, 3224.
21. For reviews on oligosaccharide synthesis including the Koenigs-Knorr approach see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155. (b) Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212. (c) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (d) Boons, G. J. Tetrahedron 1996, 52, 1095.
22. For reviews on oligosaccharide synthesis including the Koenigs-Knorr approach see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155. (b) Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212. (c) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (d) Boons, G. J. Tetrahedron 1996, 52, 1095.
23. For reviews on oligosaccharide synthesis including the Koenigs-Knorr approach see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155. (b) Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212. (c) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (d) Boons, G. J. Tetrahedron 1996, 52, 1095.
24. For reviews on oligosaccharide synthesis including the Koenigs-Knorr approach see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155. (b) Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212. (c) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (d) Boons, G. J. Tetrahedron 1996, 52, 1095.
25. Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Styliandes, N. A. J. Am. Chem. Soc. 1990, 112, 3693.
26. Boss, R.; Scheffold, R. Angew. Chem., Int. Ed. Engl. 1976, 15, 558.
27. Beig, T.; Szeja, W.; Windmüller, R.; Schmidt, R. R. Tetrahedron Lett. 1985, 4, 441.
28. Chenault, H. K.; Chafin, F. C. J. Org. Chem. 1994, 59, 6167.
29. Grattan, T. J.; Whitehurst, J. S. J. Chem. Soc., Perkin Trans. 1 1990, 11.
30. (a) Warren, C. D.; Jeanloz, R. W. Carbohydr. Res. 1977, 53, 67.
31. (b) Nashigushi, T.; Tachi, T.; Fukuzumi, K. J. Org. Chem. 1975, 40, 237.
32. (c) van Boeckel, C. A. A.; van Boom, J. H. Tetrahedron Lett. 1979, 3561.
33. Motherwell, W. B.; Powell, M. J. Chem. Soc., Chem. Commun. 1991, 1399.
34. Unpublished results from this laboratory.
35. Dewhirst, D. K. C.; Keim, W.; Reilly, C. A. Inorg. Chem. 1968, 7, 546.
36. Strauss, S. H.; Diamond, S. E.; Mares, F.; Shriver, D. F. Inorg. Chem. 1978, 17, 3064.
37. (a) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115 1580.
38. (b) Ley, S. V.; Priepke, H. W. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2292.
39. (c) Yamada, H.; Harada, T.; Miyazaki, H.; Takahashi, T. Tetrahedron Lett. 1994, 35, 3979.
40. (d) Yamada, H.; Harada, T.; Takahashi, T. J. Am. Chem. Soc. 1994, 116, 7919.
41. Weggmann, B.; Schmidt, R. R. J. Carbohydr. Chem. 1987, 6, 357.