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Updated: May 9, 2026

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Synthesis of C-septanosides from pyranoses via vinyl addition and electrophilic cyclization
1Department of Chemistry, University of Connecticut, 55 North Eagleville Road, U-3060, Storrs, Connecticut 06269, USA.
Abstract:
A two-step synthesis of C-septanosides from pyranoses is reported. Vinyl addition to tetra-O-benzyl D-glucose, D-galactose, and D-mannose gave the corresponding allylic alcohols. Electrophilic cyclization followed by treatment with iodine gave iodomethyl C-septanosides suitable for substitution reactions. The cyclizations were diastereoselective, giving cis-1,2 configured C-septanosides. Selectivity is rationalized through a model for electrophilic additions that invokes the conformation of the allylic system. This new approach should be generally applicable to the synthesis of a variety of C-septanosides.
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