Highly Stereoselective Synthesis of α-L-Olivomycosides via Trimethylsilyl Triflate Mediated Glycosidations of 1- O -Acetyl-4- O -isobutyryl-2,6-dideoxy-2-iodo-3- C -methyl-α-L-mannopyranose

Synlett

Volumn 1993, Issue 4, 1993, Pages 264-266

  Roush, William R ^a   Briner, Karin ^a   Sebesta, David P ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84913962444     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1993-22425     Document Type: Article

References (22)

1. Scbesta, D. P.; Roush, W. R. J. Org. Chem. 1992, 57, 4799.
2. Thiem, J.; Kail, H.; Schwentner, J. Synthesis 1978, 696.
3. For a summary of numerous applications of this method: Thiem, J. In "Trends in Synthetic Carbohydrate Chemistry; " Horton, D.; Hawkins, L. D.; McGarvey, G. J., Eds.; ACS Symposium Series 386, 1989, p. 131.
4. Thiem, J.; Elvers, J. Chem. Ber. 1980, 113, 3049.
5. Thiem, J.; Gerken, M. J. Org. Chem. 1985, 50, 954.
6. Friesen, R. W.; Danishefsky, S, J. J. Am. Chem. Soc. 1989, 111, 6656, and references therein.
7. Horton, D.; Priebe, W.; Sznaidman, M. Carbohydr. Res. 1990, 205, 71.
8. Suzuki, K.; Sulikowski, G. A.; Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1990, 112, 8895.
9. TMS-OTf catalyzed Helfencb-type glycosyktions: Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234.
10. Ogawa, T.; Beppu, K.; Nakabayashi, S. Carbohydr. Res. 1981, 93, C6.
11. Perez, M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 75.
12. Trumtel, M.; Tavecchia, P.; Veyrieres, A.; Sinay, P. Carbohydr. Res. 1989, 191, 29.
13. Reviews of glycosylation reactions: Paulsen, H. Angew. Chem. Int. Ed. Engl. 1982, 21, 155.
14. α-Glycosides generally are highly favored in glycosidations of substrates containing axial, non-participating C (2) heteroatom substituents (i.e., manno configuration): see ref. 7 and Bock, K.; Lundt, I.; Pedersen, C. Carbohydr. Res. 1984, 130, 125.
15. Nicolaou, K. C; Ladduwahetty, T.; Randall, J. L.; Chucholowski, A. J. Am. Chem. Soc. 1986, 108, 2466.
16. Ito, Y.; Ogawa, T. Tetrahedron Lett. 1987, 28, 6221. Roush, W. R.; Sebesta, D. P., unpublished research (ref. 9).
17. Prepared in 67% overall yield from 4-0-acetyl-3-0-(t-butyldiroethylsilyl)-6-0-tosyl-D-glucal (Crich, D.; Ritchie, T. J. Carbohydr. Res. 1990, 197, 324)
18. Prepared in 70% yield from 3-0-(t-butyl-dimethylsilyl)-6-0-tosyl-D-glucal (Crich, D.; Ritchie, T. J. Carbohydr. Res. 1990, 197, 324) by chloroacetylation with (ClOfeCOfeO and pyridine followed by desilylation with Et3NHF.
19. Eby, R.; Schuerch, C. Carbohydr. Res. 1974, 34, 79.
20. Kuster, J. M.; Dyong, I. Liebigs Ann. Chem. 1975, 2179.
21. Iiptak, A.; Jodal, L; Nanasi, P. Carbohydr. Res. 1975, 44, 1.
22. Garegg, P. J.; Hultberg, H.; Wallin, S. Carbohydr. Res. 1982, 108, 97.