Studies on glycosides - XXIV. Synthesis of a phenylpropanoid glycoside, Osmanthuside B6

摘要

2-Ac-Osmanthuside B6 [2-(4-hydroxyphenyl)ethyl 2-O-acetyl-3-O-(alpha-L-rhamnopyranosyl)-6-O-(4-hydroxycinnamoyl)-beta-D-g lucopyranoside 8], a derivative of Osmanthuside B6, was synthesized in 7 steps with the goal of preparing Osmanthuside B6. Surprisingly, it was found that the 2-acetyl group in the glucose ring of the compound 7, 1-O-[2-(4-allyloxyphenyl)ethyl]-2-O-acetyl-3-O-(2,3,4-tri-O-acetyl-alpha-L -rhamnopyranosyl)-6-O-(4-acetoxycinnamoyl)-beta-D-glucopyranoside, could not be removed by conventional deacetylation procedures. (C) 1998 Elsevier Science Ltd. All rights reserved. [References: 14]