The application belongs to the technical field of compound preparation, and discloses a preparation method of (1'S, 2'S)-
eugenol glycerol 3'-O-beta-D-glucopyranoside. The method is characterized in that: a phenolic hydroxyl group
allyl compound protected by a
benzyl group is subjected to O-
glycosylation reaction with a D-glucopyranosyl donor protected by an acetyl group, so as to obtain an olefin type protected
glycoside intermediate which retains a
side chain carbon-carbon
double bond; then, asymmetric
dihydroxylation reaction is performed on the intermediate, so as to construct a target
vicinal diol chiral structure; finally, the acetyl
protecting group of the
sugar hydroxyl group and the benzyl
protecting group of the phenolic hydroxyl group are sequentially removed, so as to obtain the target compound. The preparation method of (1'S, 2'S)-
eugenol glycerol 3'-O-beta-D-glucopyranoside is characterized in that: the
glycoside bond is constructed before
dihydroxylation, which is beneficial to reducing the competition reaction of multiple hydroxyl groups and realizing the preparation of the target compound.