Synthesis of benzophenone glucopyranosides from Phaleria macrocarpa and related benzophenone glucopyranosides.
The first total syntheses of benzophenone glucopyranosides reported from Phaleria macrocarpa and related benzophenone glucopyranosides were successfully carried out. The alkoxy groups present ortho to the carbonyl group in polyalkoxybenzophenones were selectively deprotected by AlCl(3)-PhNMe(2) in high yields, leaving other alkoxy groups unaffected. It was concluded in the current synthetic study that all the reported benzophenone glucopyranosides possessed the same structure as 2,4',6-trihydroxy-4-methoxybenzophenone 2-O-beta-D-glucopyranoside.
Hendra
Phebe
P
Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan.
Fukushi
Yukiharu
Y
Hashidoko
Yasuyuki
Y
D001577:Benzophenones / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013329:Structure-Activity Relationship; D029645:Thymelaeaceae / Q000737:chemistry*
D001577:Benzophenones; D006027:Glycosides; C047723:benzophenone