Download Carbohydrate Chemistry Volume 10 by J S Brimacombe PDF

By J S Brimacombe

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By J S Brimacombe

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Iversen, Acta Chem. Scand. (B), 1976, 30, 185. K. Hayday and R. D. McKelvey, J. Org. , 1976, 41, 2222. 117 U. Schwarzmaier, Chem. , 1976, 109, 3250. S. Hirano, M. Ishigami, and Y . Ohe, J . O r g . , 1976, 41, 4038. 12g S-GIycosides Treatment of alkyl l-thio-P-D-glucopyranosidetetra-acetates with boron trifluoride in dichloromethane at room temperature afforded mixtures of the aand 8-anomers, in the ratio of ca. lZ7Boron trifluoride also catalysed the condensation of equimolar proportions of 172-trans-related monosaccharide peresters and alkyl, alkenyl, and some aryl thiols to provide a convenient synthesis of esters S.

Oxirans are also mentioned in Chapters 14, 15, 16, and 21. -The enones (42) and (43) have been prepared by oxidation of the corresponding allylic alcohols with manganese d i 0 ~ i d e . l Whereas ~~ the oxiran derivative (44) afforded the allylic alcohol (45) on treatment with butyllithium, the Zyxo-isomer (46) gave the 2-substituted glycal (47). Enols with equatorially oriented hydroxy-groups were obtained when the enones (42) and (43) were reduced with sodium borohydride. g. Iao A. Banaszek, Bull.

R. Ingle, and J. L. Bose, Indian J. , 1976, 14B, 369 (Chem. , 1976, 85, 193 024x). L. Rosenfeld and Y . C. , 1976, 46, 155. K. Kawaguchi and N. Kashimura, Agric. and Biol. Chem. (Japan), 1976, 40, 241. E. E. Lee, G. Keaveney, A. Hartigan, and P. S . , 1976, 49, 475. -glycoside, whereas the chloroethyl derivatives (1 7), (18), and (19) yielded FH,OAc ‘ \ O--C-OCH,R I M C (16) R = Me (17) R = CH,CI (18) R = CHCl, (19) R = CCI, mixtures containing 16, 50, and 67%, respectively, of the corresponding a-glycoside.

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