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Facile synthesis of the sugar cores from phenylpropanoid glycosides

✍ Scribed by Zhong-Jun Li; He-Qing Huang; Meng-Shen Cai

Publisher
Elsevier Science
Year
1994
Tongue
English
Weight
726 KB
Volume
265
Category
Article
ISSN
0008-6215

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✦ Synopsis

Ally1 Z-O-benzoyl-4,6-O-benzylidene-a-D-glucopyranoside (3)) obtained by selective benzoylation of ally1 4,6-O-benzylidene-cY-D-glucopyranoside (2) with benzoyl chloride-imidazole in anhydrous chloroform, reacted with 2, 3, 4-tri-O-benzoyl-cy-L-rhamnopyranosyl bromide to give a disaccharide derivative (4), and an important intermediate (5) was obtained by cleavage of its acetal. Treatment of 5 with a series of glycopyranosyl bromides, protected by acetyl or benzoyl groups in benzene-nitromethane in the presence of Hg( CN), as a catalyst afforded four trisaccharides (6-9). The disaccharide (5) and trisaccharides (69) constitute the sugar cores of phenylpropanoid glycosides. A new glycosyl anomeric leaving group, trichloroacetoxy, was employed to prepare the disaccharide (4) and trisaccharides residue (8) efficiently and with high stereoselectivity.

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