74256-81-8Relevant academic research and scientific papers
Stereoselective O-Glycosylations by Pyrylium Salt Organocatalysis**
Nielsen, Michael Martin,Holmstr?m, Thomas,Pedersen, Christian Marcus
supporting information, (2021/12/30)
Despite many years of invention, the field of carbohydrate chemistry remains rather inaccessible to non-specialists, which limits the scientific impact and reach of the discoveries made in the field. Aiming to increase the availability of stereoselective
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.
Gold(III) Chloride and Phenylacetylene: A Catalyst System for the Ferrier Rearrangement, and O-Glycosylation of 1-O-Acetyl Sugars as Glycosyl Donors
Roy, Rashmi,Rajasekaran, Parasuraman,Mallick, Asadulla,Vankar, Yashwant D.
, p. 5564 - 5573 (2014/10/15)
We have developed a new catalyst system comprising AuCl3 and phenylacetylene that promotes the Ferrier rearrangement of glycals and 2-acetoxymethylglycals with different nucleophiles, and also the O-glycosylation of 1-O-acetyl sugars to obtain a variety of useful glycosides at room temperature through relay catalysis. Good anomeric selectivity was observed for the Ferrier rearrangements, whereas the O-glycosylation of 1-O-acetyl sugars gave mixtures of diastereomers with moderate to excellent selectivity.
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
α-Glucosylation of Phenols with Tetra-O-benzyl-α-D-glucose
Koto, Shinkiti,Morishima, Naohiko,Araki, Mihoko,Tsuchiya, Takuji,Zen, Shonosuke
, p. 1895 - 1896 (2007/10/02)
An α-glucosylation of phenols with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose is described.This uses a mixture of p-nitobenzenesulfonyl chloride, silver trifluoromethanesulfonate and triethylamine in dichloromethane in a two-stage treatment.
