190122-90-8Relevant academic research and scientific papers
Total synthesis of the phenylpropanoid glycoside, grayanoside A
Zhang, San-Qi,Li, Zhong-Jun,Wang, An-Bang,Meng-Shen, Cai,Feng, Rui
, p. 281 - 285 (2007/10/03)
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.
