149228-72-8Relevant academic research and scientific papers
Practical synthesis of a C-glycosyl flavonoid via O→C glycoside rearrangement
Kumazawa,Ohki,Ishida,Sato,Onodera,Matsuba
, p. 1379 - 1384 (2007/10/02)
The C-glycosylation of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride and 2-acetylphloroglucinol 3,5-bis(alkyl ether) in the presence of boron trifluoride etherate as an activator stereoselectively gave the β-C-glucoside in a good yield via O→C glycos
Aryl C-glycosides from O-glycosyltrichloroacetimidates and phenol derivatives with trimethylsilyl trifluoromethanesulfonate (TMSOTf) as the catalyst
Mahling,Schmidt
, p. 325 - 328 (2007/10/02)
The reaction of O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)trichloracetimidate (1), as glycosyl donor with phenol and naphthol derivatives 2a-d and 2f-h, as glycosyl acceptors, furnished in the presence of catalytic amounts of TMSOTf the corresponding o-hydroxyaryl C-β-D-glucopyranosides 3a-d, f-h regio- and stereoselectively. The less reactive 4-methoxyphenol (2e), α-naphthol (2i), the hydroxy substituted coumarines 2j, k and the flavone 2l afforded under these conditions O-glycosides 5e, i-l. Hydrogenolytic O-debenzylation of 3a,b,d afforded compounds 4a,b,d.
C-GLUCOSYLARENES FROM O-α-D-GLUCOSYL-TRICHLOROACETIMIDATES. STRUCTURE OF BERGENIN DERIVATIVES
Schmidt, Richard R.,Effenberger, Gunther
, p. 59 - 80 (2007/10/02)
C-Glucosylation of oxysubstituted benzene derivatives with O-α-D-glucopyranosyl trichloroacetimidate gave mainly β-D-glucopyranosylarenes.The most efficient catalysts were diethyl ether*boron trifluoride, diethyl ether*zinc chloride and zinc chloride.The
