Linker influence on the stereochemical outcome of glycosylations utilizing solid support-bound glycosyl phosphates

Organic Letters

Volumn 4, Issue 16, 2002, Pages 2751-2754

  Hunt, Diana K ^a   Seeberger, Peter H ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHATE;

ARTICLE; CHEMISTRY; GLYCOSYLATION; STEREOISOMERISM;

GLYCOSYLATION; PHOSPHATES; STEREOISOMERISM;

EID: 0037043547     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026276o     Document Type: Article

References (22)

1. (a) Solid Support Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries; Seeberger, P. H., Ed.; Wiley: New York, 2001. For recent reviews, see:
2. (b) Ito, Y.; Manabe, S. Curr. Opin. Chem. Biol. 1998, 2, 701-708.
3. Seeberger, P. H.; Haase, W.-C. Chem. Rev. 2000, 100, 4349-4393.
4. (a) Plante, O. J.; Palmacci, E. R.; Seeberger, P. H. Science 2001, 291, 1523-1527.
5. (b) Sears, P.; Wong, C. H. Science 2001, 291, 2344-2350.
6. Seeberger, P. H.; Danishefsky, S. J. Acc. Chem. Res. 1998, 31, 685-695.
7. (a) Doi, T.; Sugiki, M.; Yamada, H.; Takahashi, T. Tetrahedron Lett. 1999, 40, 2141-2144.
8. (b) Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1997, 119, 5562-5566.
9. (c) Kononov, L. O.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1997, 38, 1599-1602.
10. (d) Manabe, S.; Ito, Y. Chem. Pharm. Bull. 2001, 49, 1234-1235.
11. (e) Zhu, T.; Boons, G.-J. Angew. Chem., Int. Ed. 1998, 37, 1898-1900.
12. (a) Palmacci, E. R.; Plante, O. J.; Seeberger, P. H. Eur. J. Org. Chem. 2002, 585-589.
13. (b) Plante, O. J.; Palmacci, E. R.; Andrade, R. B.; Seeberger, P. H. J. Am. Chem. Soc. 2001, 123, 9545-9554.
14. (a) Adinolfi, M.; Barone, G.; De Napoli, L.; Iadonisi, A.; Piccialli, G. Tetrahedron Lett. 1998, 39, 1953-1956.
15. (b) Adinolfi, M.; Barone, G.; De Napoli, L.; Iadonisi, A.; Piccialli, G. Tetrahedron Lett. 1996, 37, 5007-5010.
16. (a) Excoffier, G.; Gagnaire, D.; Utille, J.-P. Carbohydr. Res. 1975, 39, 368-373.
17. (b) Excoffier, G.; Gagnaire, D. Y.; Vignon, M. R. Carbohydr. Res. 1976, 46, 201-213.
18. Tschantz, M. A.; Burgess, L. E.; Meyers, A. I. Org. Synth. 1996, 73, 215-220.
19. (a) Demchenko, A.; Stauch, T.; Boons, G. J. Synlett 1997, 7, 818-820.
20. (b) Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179.
21. Schmidt, R. R. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.
22. Thioglycoside 28 was prepared by an alternate route; see Supporting Information.