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-Science-Chemical Encyclopedia-lookchem

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
Add time:08/21/2019 Source:sciencedirect.com

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.

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