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A stereoselective synthesis of pyruvic 4,6-acetals of d-hexopyranose residues

โœ Scribed by Gerald O. Aspinall; Ibrahim H. Ibrahim; Naveen K. Khare

Publisher
Elsevier Science
Year
1990
Tongue
English
Weight
755 KB
Volume
200
Category
Article
ISSN
0008-6215

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โœฆ Synopsis

A stereoselective synthesis of pgruvic 4,6-acetals in their naturally occurring configurations on a-p-glucopyranose, a-p-mannopyranose, and /I-p-galactopyranose residues is based on the preferential formation of 4,6-[l-(3,4-dimethoxyphenyl)ethylidene] acetals bearing equatorial methyl groups. 2,3-Di-Oacyl derivatives ofthese acetals at-e oxidized with ruthenium tetraoxide to yield the corresponding 4,6-(1 -carboxyethylidene) acetals. Synthesis of ally1 4,6-O[l(~-l-methoxycarbonylethylidene]-3-~-methyl-~-~-glucopyranoside has been achieved with protection of the ally1 glycoside by epoxidation and subsequent regenerative deoxygenation with 3-methylbenzothiazols2selone. The ally1 glycoside has been subjected in sequence to saponification, ozonolysis, and reductive amination in the presence of bovine serum albumin to furnish a neoantigen.

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