74256-84-1Relevant academic research and scientific papers
An Unexpected FeCl 3/C-Catalyzed β-Stereoselective Glycosylation in the Presence of the C(2)-Benzyl Group
Guo, Hong,Li, Juan,Si, Wenshuai,Tang, Jie,Tang, Tianjun,Wang, Zhongfu,Yang, Guofang,Zhang, Jianbo
, p. 2984 - 3000 (2019/07/22)
An efficient and completely β-stereoselective glycosylation that did not rely on neighboring group participation is described using 2-20 molpercent FeCl 3 /C as the catalyst and benzylated propargyl glycosides as the donors to reach yields up to 96percent under mild condition. With an octatomic-ring intermediate at the α-face of FeCl 3 /C with alkyne of propargyl glycosides, a panel of aglycones comprising aliphatic, alicyclic, unsaturated alcohols, halogenated alcohols, and phenols with different substitution were examined successfully for the exclusive β-stereoselective glycosylation reaction.
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
Nucleophilic Substitution of Tetra-O-benzyl-α-D-glucopyranosyl 1-O-Phosphate under Phase-transfer Catalysed Conditions
Bogusiak, J.,Szeja, W.
, p. 2309 - 2314 (2007/10/02)
An efficient conversion of tetra-O-benzyl-α-D-glucopyranosyl 1-O-phosphate into corresponding 1-thiosugar derivatives, O-aryl glycosides and azides have been described.Reactions were performed under Phase-Transfer Catalysed conditions or in a Catalytic-Tw
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.
