160913-21-3Relevant academic research and scientific papers
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
Sato, Shingo,Akiya, Toshiki,Suzuki, Toshiyuki,Onodera, Jun-Ichi
, p. 2611 - 2614 (2004)
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-β-glycosylic compounds in highest total yield of 81%.
Functional Characterization and Structural Basis of an Efficient Di-C-glycosyltransferase from Glycyrrhiza glabra
Chi, Chang-Biao,He, Jun-Bin,Li, Fu-Dong,Li, Kai,Liu, Zhen-Ming,Ma, Ming,Qiao, Xue,Shi, Xiao-Meng,Su, Hui-Fei,Wang, Yu-Xi,Wang, Zi-Long,Yang, Dong-Hui,Ye, Min,Yun, Cai-Hong,Zhang, Liang-Ren,Zhang, Meng,Zhang, Zhi-Yong,Zhang, Zhong-Yi
supporting information, p. 3506 - 3512 (2020/03/06)
A highly efficient di-C-glycosyltransferase GgCGT was discovered from the medicinal plant Glycyrrhiza glabra. GgCGT catalyzes a two-step di-C-glycosylation of flopropione-containing substrates with conversion rates of >98%. To elucidate the catalytic mech
Synthesis and antihyperglycemic activity of phenolic C-glycosides
Rawat, Preeti,Kumar, Manmeet,Rahuja, Neha,Srivastava, Daya Shankar Lal,Srivastava, Arvind Kumar,Maurya, Rakesh
scheme or table, p. 228 - 233 (2011/02/27)
Various phenolic C-glycosides were evaluated for their in vitro and in vivo antihyperglycemic activity employing glucose uptake by rat muscle cell lines (L-6) and low dosed-streptozotocin-induced diabetic rats, respectively. Some of phenolic C-glycosides were isolated from Pterocarpus marsupium and Ulmus wallichiana and other were synthesized by unprotected sugar and phloroacetophenone using Sc(OTf)3 in aqueous ethanol. Eight among tested compounds showed significant lowering of blood glucose level on low dosed-streptozotocin-induced diabetic rats. The compound 24 lowered the blood glucose levels by 34.9% and 33.6% during 0-5 h and 0-24 h, respectively, at the dose of 25 mg/kg body weight which is comparable to standard antidiabetic drug metformin.
Total synthesis of two isoflavone bis-C-glycosides: Genistein and orobol 6,8-Di-C-β-D-glucopyranosides
Sato, Shingo,Ishikawa, Hidetoshi
body text, p. 3126 - 3130 (2010/11/04)
This paper describes the first successful synthesis of two isoflavone bis-C-glycosides, genistein and orobol 6,8-di-C-β-D-glucopyranosides from phloroacetophenone bis-C-glycoside in total yields of 27 and 19%, respectively, using a four-step reaction: dir
Cleavage of the C-C linkage between the sugar and the aglycon in C-glycosylphloroacetophenone, and the NMR spectral characteristics of the resulting di-C-glycosyl compound
Kumazawa,Kimura,Matsuba,Sato,Onodera
, p. 207 - 213 (2007/10/03)
The treatment of unprotected mono-C-β-D-glucopyranosylphloroacetophenone with a cation-exchange resin in anhydrous acetonitrile afforded both a phloroacetophenone and a di-C-β-D-glucopyranosylphloroacetophenone. Treatment of an unprotected mono-C-(2-deoxy-β-D-arabino-hexopyranosyl)phloroacetophenone (mono-C-2-deoxy-β-D-glucopyranosylphloroacetophenone) also afforded both the aglycon and di-C-(2-deoxy-β-D-arabino-hexopyranosyl)phloroacetophenone. The reaction mixtures were acetylated, and the structures of the isolated products were determined by NMR spectroscopy. This is the first demonstration of the formation of a di-C-glycosyl compound during the chemical cleavage of the C-C linkage between the sugar and the aglycon in an aryl C-glycosyl derivative.
