THE ALPHA AND BETA 1,3,4,6-TETRAACETYL-D-GLUCOPYRANOSES AND THEIR CHLOROACETYL DERIVATIVES

Abstract

Reaction of 3,4,6-triacetyl-β-D-glucopyranosyl chloride with silver acetate in acetic acid gave 1,3,4,6-tetraacetyl-α-D-glucopyranose, m.p. 97–98 °C., [α]D + 145° (chloroform). 3,4,6,-Triacetyl-α-D-glucopyrartosyl chloride, m.p. 93–94 °C., [α]D + 185° (chloroform), prepared from the β-anomer by isomerization in acetone, with silver acetate in acetic acid gave 1,3,4,6-tetraacetyl-β-D-glucopyranose, m.p. 137–138 °C., [α]D + 26° (chloroform). The structures of these glucose tetraacetates were established by the interconversion of chloroacetyl derivatives.