Carbohydrate Research p. 281 - 285 (1997)
Update date:2022-07-30
Topics:
Zhang, San-Qi
Li, Zhong-Jun
Wang, An-Bang
Meng-Shen, Cai
Feng, Rui
Grayanoside A, 2-(4-hydroxyphenyl)ethyl 6-O-feruloyl-β-D-glucopyranoside, was synthesized for the first time by using chloroacetyl groups for the protection of hydroxy functions. 2-(4-Allyloxyphenyl)ethyl 4-O-[(4-O-allyl)feruloyl]-2,3,6-tri-O-chloroacetyl-β-D-glucopyranoside (12) was synthesized from 2-(4-allyloxyphenyl)ethyl 4,6-O-benzylidene-β-D-glucopyranoside (8) in four steps with the goal of preparing syringalide B. It was found, however, that the feruloyl group migrated from the 4- to the 6-position of the glycopyranoside during the deprotection of 12.
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(1997)