A new efficient glycosylation method employing glycosyl pentenoates and PhSeOTf

Tetrahedron Letters

Volumn 47, Issue 52, 2006, Pages 9191-9194

  Choi, Tae Jin ^a   Baek, Ju Yuel ^a   Jeon, Heung Bae ^a   Kim, Kwan Soo ^a  

^a Yonsei University   (South Korea)

Author keywords

Glycoside; Glycosyl pentenoate; Glycosylation; Phenylselenyl triflate

Indexed keywords

2,3,4,6 TETRA O BENZYL DEXTRO MANNOPYRANOSYLPENTENOATE; ALCOHOL; CARBOHYDRATE DERIVATIVE; DISACCHARIDE; GLUCOSE; MANNOSE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; GLYCOSYLATION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

TETRA;

EID: 33751163239     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.158     Document Type: Article

References (27)

1. Varki A. Glycobiology 3 (1993) 97
2. Dwek R.A. Chem. Rev. 96 (1996) 683
3. Bertozzi C.R., and Kiessling L.L. Science 291 (2001) 2357
4. Schmidt R.R., and Kinzy W. Adv. Carbohydr. Chem. Biochem. 50 (1994) 21
5. Schmidt R.R. In: Khan S.H., and O'Neil R.A. (Eds). Modern Methods in Carbohydrate Synthesis (1996), Harwood Academic, Amsterdam 20-54
6. Garegg P.J. Adv. Carbohydr. Chem. Biochem. 52 (1997) 179
7. Kahne D., Walker S., Cheng Y., and Engen D.V. J. Am. Chem. Soc. 111 (1989) 6881
8. Danishefsky S.J., and Bilodeau M.T. Angew. Chem., Int. Ed. 35 (1996) 1380
9. Fraser-Reid B., and Madsen R. In: Hanessian S. (Ed). Preparative Carbohydrate Chemistry (1997), Marcel Dekker, New York 339-356
10. Shimizu M., Togo H., and Yokoyama M. Synthesis (1998) 799
11. Plante O.J., Andrade R.B., and Seeberger P.H. Org. Lett. 1 (1999) 211
12. For recent examples of new glycosyl donors and activating systems, see:. Plante O.J., Palmacci E.R., Andrade R.B., and Seeberger P.H. J. Am. Chem. Soc. 123 (2001) 9545
13. Hinklin R.J., and Kiessling L.L. J. Am. Chem. Soc. 123 (2001) 3379
14. Davis B.J., Ward S.J., and Rendle P.M. Chem. Commun. (2001) 189
15. Petersen L., and Jensen K.J. J. Org. Chem. 66 (2001) 6268
16. Nguyen H.M., Chen Y., Duron S.G., and Gin D.Y. J. Am. Chem. Soc. 123 (2001) 8766
17. Hadd M.J., and Gervay J. Carbohydr. Res. 320 (1999) 61
18. Crich D., and Sun S. J. Am. Chem. Soc. 120 (1998) 435
19. Crich D., and Smith M. J. Am. Chem. Soc. 123 (2001) 9015
20. Kim K.S., Kim J.H., Lee Y.J., Lee Y.J., and Park J. J. Am. Chem. Soc. 123 (2001) 8477
21. Kim K.S., Park J., Lee Y.J., and Seo Y.S. Angew. Chem., Int. Ed. 42 (2003) 459
22. Lee Y.J., Lee K., Jung E.H., Jeon H.B., and Kim K.S. Org. Lett. 7 (2005) 3263
23. Kunz H., Wernig P., and Schultz M. Synlett (1990) 631
24. Lopez J.C., and Frazer-Reid B. J. Chem. Soc., Chem. Commun. (1991) 159
25. Baek J.Y., Choi T.J., Jeon H.B., and Kim K.S. Angew. Chem., Int. Ed. 45 (2006) 7436
26. Crich D., Smith M., Yao Q., and Picione J. Synthesis (2001) 323
27. 2, 4:1:1) to afford the desired mannopyranoside 10 (92%, α/β = 1.1:1).