Chemoenzymatic synthesis of sacranosides A and B

Abstract

Direct β-glucosidation between (-)-myrtenol and nerol and D-glucose (3) using the immobilized β-glucosidase from almonds with the synthetic prepolymer ENTP-4000 gave myrtenyl O-β-D-glucoside (4) and neryl O-β-D-glucoside (10), respectively. The coupling of the myrtenyl or neryl O-β-D-glucopyranoside congeners (7 or 13) and 2,3,4-tri-O-benzoyl-β-L- arabinopyranosyl bromide (8) afforded the coupled products (9 or 14), respectively. Deprotection of the coupled products (9 or 14) afforded the synthetic myrtenyl 6-O-α-L-arabinopyranosyl-β-D-glucopyranoside (Sacranoside A, 1) or neryl 6-O-α-L-arabinopyranosyl-β-D- glucopyranoside (Sacranoside B, 2), respectively. © 2006 Pharmaceutical Society of Japan.