CHEMOENZYMATIC SYNTHESIS OF NATURALLY OCCURRING PHENETHYL (l->6)-beta-D-GLUCO-PYRANOSIDES

摘要

Direct beta-glucosidation between phenethyl alcohol and D-glucose (5) using the immobilized beta-glucosidase from almonds with the synthetic prepolymer ENTP-4000 gave a phenethyl beta-D-glucoside (1) in 34% yield.The coupling of the phenethyl O-beta-D-glucopyranoside congener (8) and methylthio-2,3,4-tri-O-acetyl-beta-D-xylopyranoside (9),2,3,4-tri-O-acetyl-alpha-L-arabinopyranosyl bromide (11),and methylthio 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranoside (13) afforded the coupled products (10,12,and 14),respectively.Deprotection of the coupled products (10,12,and 14) afforded the synthetic phenethyl O-beta-D-xylopyranosy-(l->6)-beta-D- glucopyranoside (2),phenethyl O-alpha-L-arabinopyranosy-(l->6)-beta-D-glucopyranoside (3),and phenethyl O-alpha-L-rhamnopyranosy- (1->6)-beta-D-glucopyranoside (4),respectively.