Total Synthesis of Monosaccharides. Synthesis of Methyl DL-Pentopyranosides with α- and β-lyxo, β-ribo, α-xylo, and α-arabino Configurations from Furfuryl Alcohol

Abstract

Hydroxylation and epoxidation, followed by the oxirane ring opening, of methyl 2,3-dideoxy-α and β-DL-pent-2-enopyranosides, readily available by the transformation of furfuryl alcohol, afforded the title compounds. Steric course of hydroxylation and epoxidation reactions were examined. The p.m.r. data of methyl 4-O-acetyl-2,3-anhydro-DL-pentopyranosides are reported.