Carbohydrate Chemistry

Effect of Protecting Groups and Solvents in Anomeric O-Alkylation of Mannopyranose1

J Tamura, RR Schmidt

Index: Tamura, Junichi; Schmidt, R. R. Journal of Carbohydrate Chemistry, 1995 ,  vol. 14,  # 7  p. 895 - 912

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Citation Number: 13

Abstract

Abstract Anomeric O-alkylation of mannopyranoses with various protecting groups was investigated using mannose derivatives and 2, 3-O-isopropylidene-lO-trifluoro- methanesulfonyl-D-glycerol (1) as alkylating agent. Generally, in polar solvents higher α/β ratios were obtained than in nonpolar solvents. Sterically demanding protecting groups at the 6-O-position and polar solvents led to higher yields. Reactivity differences were ...