41671-26-5Relevant academic research and scientific papers
Aryl C-glycosides from O-glycosyltrichloroacetimidates and phenol derivatives with trimethylsilyl trifluoromethanesulfonate (TMSOTf) as the catalyst
Mahling,Schmidt
, p. 325 - 328 (1993)
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.
Selective formation of β-O-aryl glycosides in the absence of the C(2)-ester neighboring group
McKay, Matthew J.,Naab, Benjamin D.,Mercer, Gregory J.,Nguyen, Hien M.
supporting information; experimental part, p. 4705 - 4711 (2009/09/30)
(Chemical Equation Presented) The development of a general and practical method for the stereoselective synthesis of β-O-aryl glycosides that exploits the nature of a cationic palladium(II) catalyst, instead of a C(2)-ester directing group, to control the
New Synthetic Methods and Reagents for Complex Carbohydrates. IX. Aryl D-Glucopyranosides and 1-Aryl-1-deoxy-D-glucopyranoses from 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl Dimethylphosphinothioate
Yamanoi, takashi,Fujioka, Ayumi,Inazu, Toshiyuki
, p. 1488 - 1491 (2007/10/02)
The reactions of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl dimethylphosphinothioate and phenolic compounds gave the corresponding aryl α-D-glucopyranosides predominantly in good yields, even when the trimethylsiloxy derivatives of benzene, which are known
