129192-89-8Relevant academic research and scientific papers
A stereoselective synthesis of pyruvic 4,6-acetals of D-hexopyranose residues
Aspinall, Gerald O.,Ibrahim, Ibrahim H.,Khare, Naveen K.
, p. 247 - 256 (2007/10/02)
A stereoselective synthesis of pyruvic 4,6-acetals in their naturally occuring configurations on α-D-glucopyranose, α-D-mannopyranose, and β-D-galactopyranose residues is based on the preferential formation of 4,6- 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--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.
