Eutigoside A, 2-(4-hydroxyphenyl) ethyl-6-O-coumaroyl-β-D- glucopyranoside, was synthesized for the first time. 2-(4- Allyloxyphenyl) ethyl-4-O-(4-O-acetyl) coumaroyl-2, 3, 6-tri-O-acetyl- β-D-glucopyranoside (10) was synthesized from 2-O-(4-allyloxy- phenyl) ethyl-β-D-glucopyranoside (3) in 5 steps with the aim of the synthesis of Osmanthuside A. It was found surprisingly that the coumaroyl group migrated from the 4- to 6-position of the glucopyranoside during the deacetylation of 10 with NH~3/MeOH.

Key words: GLYCOSIDE, PYRANE P, PYRANE P, TOTAL SYNTHESIS, GLYCOSYLATION