163356-59-0Relevant academic research and scientific papers
Glycosyl Imidates, 70. - Synthesis of a Coumarin C-Glucoside
Mahling, Juergen-Andreas,Schmidt, Richard R.
, p. 467 - 470 (2007/10/02)
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 deg C.Deprotonation yielded the coumarin 8-C-glycoside 8, a dimethyl ether of an isomer of naturally occurring coumarin 6-C-glycosides. - Key Words: Glycosides / Carbohydrates / Trichloroacetimidates / Coumarin derivatives / Fries rearrangement / Perkin reaction / Wittig reaction
