Environmentally friendly C-glycosylation of phloroacetophenone with unprotected D-glucose using scandium(III) trifluoromethanesulfonate in aqueous media: key compounds for the syntheses of mono- and di-C-glucosylflavonoids.
The direct C-glycosylation of phloroacetophenone with an unprotected d-glucose in aqueous media using scandium(III) trifluoromethanesulfonate (Sc(OTf)3) as the catalyst, gave mono- and bis-C-beta-glycosylic compounds in highest total yield of 81%. The second and third use of the recovered Sc(OTf)3 afforded them in total yields of 56% and 53%, respectively.
Sato
Shingo
S
Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan. shingo-s@yz.yamagata-u.ac.jp
Akiya
Toshiki
T
Suzuki
Toshiyuki
T
Onodera
Jun-ichi
J
D005419:Flavonoids / Q000138:chemical synthesis*; D006031:Glycosylation; D012997:Solvents; D014867:Water
C421808:C-glucosylflavone; D005419:Flavonoids; D012997:Solvents; D014867:Water