Solution-Phase Hexasaccharide Synthesis Using Glucosyl Iodides

Organic Letters

Volumn 4, Issue 12, 2002, Pages 2039-2042

  Lam, Son N ^a   Gervay Hague, Jacquelyn ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

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ARTICLE;

EID: 0001410949     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025887d     Document Type: Article

References (41)

1. Fischer, F. Chem. Ber. 1893, 26, 2400.
2. Köenigs, W.; Knorr, E. Chem. Ber. 1901, 34, 957.
3. Helferich, B.; Ost, W. Chem. Ber. 1962, 95, 2612.
4. Lemieux, R. U.; Hendricks, K. B.; Stick, R. V.; James, K. J. Am. Chem. Soc. 1975, 97, 4056.
5. Paulsen, H.; Kolar, C. Chem. Ber. 1981, 114, 306.
6. Schmidt, R. R.; Michel, J. Angew. Chem. 1980, 92, 763. Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-123.
7. Schmidt, R. R.; Michel, J. Angew. Chem. 1980, 92, 763. Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-123.
8. Kahne, D.; Walker, S.; Cheng, Y.; Van Engen, D. J. Am. Chem. Soc 1989, 111, 6881.
9. Danishefsky, S. J.; McClure, K. F.; Randolph, J. T.; Ruggeri, R. B. Science 1993, 260, 1307.
10. (a) Plante, O. J.; Palmacci, E. R.; Andrade, R. B.; Seeberger, P. H. J. Am. Chem. Soc. 2001, 123, 9545.
11. (b) Hewitt, M. C.; Seeberger, P. H. J. Org. Chem. 2001, 66, 4233.
12. (c) Plante, O. J.; Andrade, R. B.; Seeberger, P. H. Org. Lett. 1999, 1, 211.
13. (d) Plante, O. J.; Seeberger, P. H. J. Org. Chem. 1998, 63, 9150.
14. Garegg, P. I. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179-205. Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Baasov, T.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 734. Barresi, F.; Hindsgaul, O. J. Carbohydr. Chem. 1995, 14, 1043. Ernst, B., Hart, G. W., Sinäy, P., Eds.; Carbohydrates in Chemistry and Biology; Part I, Chemistry of Saccharides; Volume 1, Chemical Syntheses of Glycosides and Glycomimetics; Wiley-VCH: Weinheim, 2000.
15. Garegg, P. I. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179-205. Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Baasov, T.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 734. Barresi, F.; Hindsgaul, O. J. Carbohydr. Chem. 1995, 14, 1043. Ernst, B., Hart, G. W., Sinäy, P., Eds.; Carbohydrates in Chemistry and Biology; Part I, Chemistry of Saccharides; Volume 1, Chemical Syntheses of Glycosides and Glycomimetics; Wiley-VCH: Weinheim, 2000.
16. Garegg, P. I. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179-205. Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Baasov, T.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 734. Barresi, F.; Hindsgaul, O. J. Carbohydr. Chem. 1995, 14, 1043. Ernst, B., Hart, G. W., Sinäy, P., Eds.; Carbohydrates in Chemistry and Biology; Part I, Chemistry of Saccharides; Volume 1, Chemical Syntheses of Glycosides and Glycomimetics; Wiley-VCH: Weinheim, 2000.
17. Garegg, P. I. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179-205. Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Baasov, T.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 734. Barresi, F.; Hindsgaul, O. J. Carbohydr. Chem. 1995, 14, 1043. Ernst, B., Hart, G. W., Sinäy, P., Eds.; Carbohydrates in Chemistry and Biology; Part I, Chemistry of Saccharides; Volume 1, Chemical Syntheses of Glycosides and Glycomimetics; Wiley-VCH: Weinheim, 2000.
18. (a) Bhat, A. S.; Gervay-Hague, J. Org. Lett. 2001, 3, 2081.
19. (b) Hadd, M. J.; Gervay, J. Carbohydr. Res. 1999, 320, 61.
20. (c) Gervay, J. Org. Synth.: Theory Appl. 1998, 4, 121-153.
21. (d) Gervay, J.; Hadd, M. J. J. Org. Chem. 1997, 62, 6961.
22. (a) Schmid, U.; Waldmann, H. Liebigs Ann./Relc. 1997, 2573.
23. (b) Tanaka, H.; Sakamoto, H.; Sano, A.; Nakamura, S.; Nakajima, M.; Hashimoto, S. Chem. Commun. 1999, 1259.
24. (c) Caputo, R.; Kunz, H.; Dominico, M.; Palumbo, G.; Pedatella, S.; Solla, F. Eur. J. Org. Chem. 1999, 3147.
25. Thiem, J.; Meyer, B. Chem. Ber. 1980, 113, 3075.
26. Chervin, S. M.; Abada, P.; Koreeda, M. Org. Lett. 2000, 2, 369.
27. (a) Lemieux, R. U.; Hayami, J. I. Can. J. Chem. 1965, 43, 2162.
28. (b) Lemieux, R. U.; Driguez, H. J. Am. Chem. Soc. 1975, 97, 4069.
29. Pasetto, P.; Chen, X.; Drain, C. M.; Franck, R. W. Chem. Commun. 2001, 81-82. Yang, G.; Franck, R. W.; Bittman, R.; Samadder, P.; Arthur, G. Org. Lett. 2001, 3, 197-200 and references therein.
30. Pasetto, P.; Chen, X.; Drain, C. M.; Franck, R. W. Chem. Commun. 2001, 81-82. Yang, G.; Franck, R. W.; Bittman, R.; Samadder, P.; Arthur, G. Org. Lett. 2001, 3, 197-200 and references therein.
31. Taylor, R. J. K. Chem. Commun. 1999, 217-227 and references
32. Yang, G.; Ding, X.; Kong, F. Tetrahedron Lett. 1997, 38, 6725.
33. This sequence of reactions has been performed on large scale (20 g).
34. 6) δ 6.78, d, J = 3.3 Hz.
35. Jung, M. E.; Lyster, M. A. J. Org. Chem. 1977, 42, 3761.
36. 3).
37. 3).
38. Araki, Y.; Endo, T.; Tanji, M.; Nagasawa, J.; Ishido, Y. Tetrahedron Lett. 1987, 28, 5853.
39. Axon, J. R.; Beckwith, A. L. J. J. Chem. Soc., Chem. Commun. 1995, 549.
40. 3).
41. 13C δ 127 ppm (C-1).