SYNTHESIS OF L-NOGALOSE AND ITS ENANTIOMER

Article abstract of DOI:10.1016/S0008-6215(00)84691-1

L-Nogalose (6-deoxy-3-C-methyl-2,3,4-tri-O-methyl-L-mannopyranose) and its enantiomer were synthesized via (a) introduction of the C-methyl branch by successive epoxidation and reduction of methyl 3,6-dideoxy-2,4-di-O-methyl-3-C-methylene-α-L-arabino-hexopyranoside, and (b) deoxygenation at C-6 of methyl 4,6-O-benzylidene-3-C-methyl-2-O-methyl-α-D-mannopyranoside, and O-methylation of the product.