Conversion of d́-glucose to methyl α-Daltropyranoside derivatives

Abstract

A novel synthesis of methyl α-D-altropyranoside derivatives 5 aid 6 has been achieved starting from methyl α-D-glucopyranoside (1). The action of tosyl chloride in pyridine on compound 1 afforded the 2,6-di-O-tosyl derivative 2 which was further treated with sodium acetate in N,N-dimethylformamide to give the 6-O-acetyl derivative 3. Treatmen of 3 with aqueous potassium hydroxide gave the methyl α-D-altropyranoside (5) which was subsequently acetylated to afford the corresponding peracetylated derivative 6.