Tetrahedron: Asymmetry

Chemoenzymatic syntheses of naturally occurring β-glucosides

H Akita, K Kurashima, T Nakamura, K Kato

Index: Akita, Hiroyuki; Kurashima, Katsumi; Nakamura, Takuya; Kato, Keisuke Tetrahedron Asymmetry, 1999 , vol. 10, # 12 p. 2429 - 2439

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Citation Number: 24

Abstract

Enzymatic glycosidation of the various kinds of primary alcohols 5, 7, 9, 11, 13 and 15 and 4- nitrophenyl-β-d-glucopyranoside 4 using β-glucosidase from almonds gave stereoselectively β-d-glucosides 6, 8, 10, 12, 14 and 16 including the naturally occurring β- glucosides in moderate yield. Among them, the β-glucosides 6, 8 and 10 were converted to the cyanoglycosides, rhodiocyanoside A 20a, osmaronin 24a and sutherlandin 29, ...