阿司匹林D-吡喃葡萄糖酯的合成

SYNTHESIS OF D-GLUCOPYRANOSYL ASPIRIN ESTERS

由2,3,4,6-四-O-乙酰-α-D-D-吡喃葡萄糖溴化物(A)和芳香酸合成1-O-芳酰-β-D-吡喃葡萄糖2,3,4,6-四乙酸酯(1～7)。产物的构型由 IR 和~1HNMR 测定。2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖(B)和芳香酰氯缩合反应的产物为1-O-芳酰-2,3,4,6-四-O-苄基-D-吡喃葡萄糖α-体和β-体的混合物,其中α组分占优势。

1-O-Aroyl-β-D-glucopyranose 2,3,4,6-tetraacetates(1～7)were obtained by the condensation of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide with aromatic acids in K_2CO_3-Me_2CO.Exclusive production of β-D-anomers was confirmed by measurements of specific rotation,IR and ~1HNMR spectra.A series of 1-O-aroyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoses were obtained as the anomeric mixture(rich in α-anomer)by condensation of the appropriate aroma- tic acid chlorides with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose.