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Glycosyl imidates, 70. Synthesis of a coumarin C ‐glucoside
Author(s) -
Mahling JürgenAndreas,
Schmidt Richard R.
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199519950363
Subject(s) - chemistry , acetic anhydride , glycosyl , glycoside , formylation , trimethylsilyl , coumarin , yield (engineering) , trimethylsilyl trifluoromethanesulfonate , wittig reaction , trifluoromethanesulfonate , aryl , stereochemistry , organic chemistry , catalysis , alkyl , materials science , metallurgy
3,5‐Dimethoxyphenol ( 2 ) was glycosylated with O ‐(2,3,4,6‐tetra‐ O ‐benzyl‐α‐ D ‐glucopyranosyl) trichloroacetimidate ( 1 ) and trimethylsilyl triflate (TMSOTf) as the promoter to yield the aryl C ‐glycoside 3 via an O ‐glycoside intermediate and subsequent Fries rearrangement. After formylation, the coumarin C ‐glycoside 7 was synthesized either by Perkin reaction with acetic anhydride or by Wittig reaction followed by cyclization at 150°C. Deprotonation yielded the coumarin 8‐ C ‐glycoside 8 , a dimethyl ether of an isomer of naturally occurring coumarin 6‐ C ‐glycosides.