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K . V. Bhat, and W. W. Zorbach : Carbohydrate Res. 10, 197 (1969). 16) Bhat, 14. , and W. W. Zorbaeh: Carbohydrate ires. 6, 63 (1968). , and I. Hayashi: Seikagaku 32, 536 (1960); Chem. Abstr. 60, 4228 (1964). , H. Ando, Y. Takahashi, H. Ono, and T. Sato: Nippon Kagaku Zasshi 85, 142 (1964) ; Chem. Abstr. 62, 623 (1965). , M . Cern#, J. Kor 426 Newer Observations on the Synthesis of O-Glycosides x9) Anet, E. F, L. J. : Carbohydrate Res. 8, 164 (1968). 2o) Clayton, C. , and N . A . Hughes: Carbohydrate Res.
H. Ott : Chem. BBer. 95, 30S6 (I962); b) Wolfrom, M . , a n d K. Koizumi : J. Org. Chem. , u. J. Zirner: Chem. Bet. 95, 2604 (1962). - Ferrier, R. , a n d D. Prasad: J. Chem. Soc. 7429 (1985). al) Wolfrom, M . , A . O. Fitter, altd L C. Gillam : Proe. Natl. Acad. Sci. S. 47, 7OO (1961). u2 a) Khorlin, A . , A . F. Bochhov, L. V. Bakinovshii u. N. K . Kochetkov : Dokl. Akad. Nauk. , ,4. Wagner, D. G~issel u. H. Oft: Chem. Bet. 95, 3064 (1962). ca) Austin, P. , F. E. Hardy, J. G. Buchanan, a n d J .
Further, additions to intermediate 2-nitrosoglycals are believed to result in the very high stereospecificity noted in the reaction of the dimeric adduct (24) with alcohols, the nucleophiles attacking C-1 from the axial side which is sterically more accessible and which is favoured for stereoelectronic reasons also 9o). 422 N e w e r O b s e r v a t i o n s on the S y n t h e s i s of O-Glycosides 2. Rearrangement Reactions The finding that alcohols react with tri-0-acetyl-D-glucal in the presence of Lewis acids to give 2,3-tmsaturated glycoside derivatives (28) has opened a new route to the synthesis of complex glycosides, since the reagents condense in equimolar proportions and give a-products with ca.