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1. Synthesis of phenyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-1-thio-α,β-l-xylo-hexopyranoside. A glycosyl donor for axenose

Author

Luca Failli, Garry R. Smith, Frank J. Villani, and Robert M. Giuliano

Subjects
Polyketomycin, Methyl glycoside, Chemistry, Organic Chemistry, Thio, Medicinal chemistry, Catalysis, Inorganic Chemistry, chemistry.chemical_compound, Trimethylsilyl trifluoromethanesulfonate, Reagent, Physical and Theoretical Chemistry, Sugar, Glycosyl donor, Oligosaccharide synthesis
Abstract

A new synthesis of the methyl-branched sugar axenose is described. Axenose is found in the antibiotics axenomycin, dutomycin, and polyketomycin. The synthesis is based on additions of organometallic reagents to pentodialdo-1,4-furanosides and allows the preparation of derivatives of methyl α- l -axenoside which are protected at the tertiary C-3 hydroxyl group. Conversion to thioglycoside derivatives for use in oligosaccharide synthesis was carried out directly from the methyl glycoside by treatment with phenylthiotrimethylsilane and trimethylsilyl trifluoromethanesulfonate.

Published
2000
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