Synthesis of naturally occurring β-D-glycopyranosicle based on a combination of immobilized β-glucosidase and metal catalyst

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For the purpose of synthesis of naturally occurring β-D-glucopyranoside, direct β-glucosidation for the many kinds of functionalized primary alcohol in the presence of D-glucose using native or immobilized β-glucosidase (EC 3.2.1.21) from almonds under kinetically or equilibrium controlled condition was carried out. The utilization of high concentration of the alcohol acceptors using the immobilized enzyme gave the corresponding [β-D-glucopyranosides, which were converted to naturally occurring β-D-glucopyranosides. Moreover, allyl (β-D-glucopyranoside obtained based on direct β-glucosidation between allyl alcohol and D-glucose using the immobilized β-glucosidase was converted to the corresponding tetraacetate, which was subjected to the Pd(II)-catalyzed Mizoroki-Heck type reaction with the substituted arylboronic acid congeners to afford the naturally occurring phenylpropenoid β-D-glucopyranosides. In the same way, the Pd(II)-catalyzed Mizoroki-Heck type reaction of allyl 6-O-glycosyl-β-D-glucopyranosides with the substituted arylboronic acid congeners gave the naturally occurring phenylpropenoid 6-O-glycosyl-β-D- glucopyranosides.