Abstract
A stereoselective synthesis of pyruvic 4,6-acetals in their naturally occurring configurations on α- d-glucopyranose, α- d-mannopyranose, and β- d-galactopyranose residues is based on the preferential formation of 4,6-[1-(3,4-dimethoxyphenyl)ethylidene] acetals bearing equatorial methyl groups. 2,3-Di- O-acyl derivatives of these acetals are oxidized with ruthenium tetraoxide to yield the corresponding 4,6-(1-carboxyethylidene) acetals. Synthesis of allyl 4,6- O[1( S)-1-methoxycarbonylethylidene]-3- O-methyl-β- d-glucopyranoside has been achieved with protection of the allyl glycoside by epoxidation and subsequent regenerative deoxygenation with 3-methylbenzothiazole-2-selone. The allyl 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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