Journal
SYNLETT
Volume -, Issue 5, Pages 785-789Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-2007-970751
Keywords
exo-glycal; 1-C-vinyl-glycopyranose; S(N)1 '-type substitution; trimethylsilyl trifluoromethanesulfonate
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This paper describes a novel synthetic approach to exo-glycals from 1-C-vinyl-D-glycopyranose derivatives via the S(N)1'-type substitution mechanism. The reaction of the 2,3,4,6-tetra-O-benzyl-1-C-vinyl-alpha-D-glycopyranose derivatives with several trimethylsilylated nucleophiles was investigated. The reactions in dichloromethane-acetonitrile (1: 1) at -78 degrees C in the presence of 20 mol% trimethylsilyl trifluoromethanesulfonate using allyltrimethylsilane and silyl enol ethers as the nucleophiles stereoselectively afforded the Z-exo-glycal derivatives in good yields.
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