Highly Stereoselective Approaches to α- and β-C-Glycopyranosides

Journal of the American Chemical Society

Volumn 104, Issue 18, 1982, Pages 4976-4978

  Lewis, Michael D ^a   Cha, Jin Kun ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845554860     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00382a053     Document Type: Article

References (24)

1. For examples, see: McDonald, F. J.; Campbell, D. C.; Vanderah, D. J.; Schmitz, F. J.; Washecheck, D. M.; Burks, J. E.; van der Helm, D. J. Org. Chem. 1975, 40, 665.
2. Connor, D. T.; Greenough, R. C.; von Strandtmann, M. J. Org. Chem. 1977, 42, 3664; 1978, 43, 5027.
3. Shulman, M. L.; Shiyan, S. D.; Khorlin, A. Y. Carbohydr. Res. 1974, 33, 229.
4. Cerretti, D. Carbohydr. Res. 1981, 94, C10.
5. Chmielewski, M.; BeMiller, J. N.; Cerretti, D. P. Carbohydr. Res. 1981, 97, C1.
6. Fraser-Reid, B.; Dawe, R. D.; Tulshian, D. B. Can. J. Chem. 1979, 57, 1746.
7. Ireland, R. E.; Thaisrivongs, S.; Vanier, N.; Wilcox, C. S. J. Org. Chem. 1980, 45, 48.
8. Hanessian, S.; Liak, T. J.; Dixit, D. M. Carbohydr. Res. 1981, 88, C14.
9. Pougny, J.-R.; Nassr, M. A. M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1981, 375.
10. Dawe, R. D.; Fraser-Reid, B. Chem. Soc., Chem. Commun. 1981, 1180 and references cited therein. See also ref 2 above.
11. Uemura, D.; Ueda, K.; Hirata, Y.; Naoki, H.; Iwashita, T. Tetrahedron Lett. 1981, 2781.
12. Moore, R. E.; Bartolini, G. J. Am. Chem. Soc. 1981, 103, 2491.
13. For an example: “Anomeric Effect: Origin and Consequences”; Szarek, W. A., Horton, D., Eds.; American Chemical Society: Washington, D.C., 1979; ACS Symp. Ser. No. 87.
14. C-Nucleoside precursors have been made by a similar approach; however, this is not strictly orbital control solely by the ring oxygen. Ogawa, T.; Pernet, A. G.; Hanessian, S. Tetrahedron Lett. 1973, 3543.
15. Deoxygenated pyrans have also been made by a similar approach from oxonium ions derived from acetylated glycals. The additions are primarily from the axial direction, although the ratios are at best 4:1: Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180.
16. Recently such an oxonium ion was observed to add hydride axially through intramolecular reaction. Deslongchamps, P.; Rowan, D. D.; Rothier, N. Can. J. Chem. 1981, 59, 2787.
17. Glaudemans, C. P. J.; Fletcher, H. G., Jr. Methods Carbohydr. Chem. 1972, 6, 373.
18. Prepared by Swern oxidation [Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480] of 1.
19. 3SiH and acids are known to reduce acetals, hemiacetals, and some alcohols; for example, see: Frainnet, E.; Esclamadon, C. C. R. Hebd. Seances Acad. Sci. 1962, 254, 1814.
20. Doyle, M. P.; DeBruyn, D. J.; Kooistra, D. A. J. Am. Chem. Soc. 1972, 94, 3659.
21. Adlington, M. G.; Orfanopoulos, M.; Fry, J. L. Tetrahedron Lett. 1976, 2955.
22. Fieser, M.; Fieser, L. F. “Reagents for Organic Synthesis”; Wiley-Interscience: New York, 1972; Vol. 3, p 172.
23. 2Br/NaH/THF-DMF/room temperature) of 1,6-anhydroglucose [Ward, R. B. Methods Carbohydr. Chem. 1963, 2, 394.
24. Coleman, G. H. Methods Carbohydr. Chem. 1963, 2, 397.