42822-03-7Relevant academic research and scientific papers
Stereoselective β-mannosylations and β-rhamnosylations from glycosyl hemiacetals mediated by lithium iodide
McGarrigle, Eoghan M.,Pepe, Dionissia A.,Pongener, Imlirenla,Ruddy, Joseph J.
, p. 10070 - 10075 (2021/08/04)
Stereoselective β-mannosylation is one of the most challenging problems in the synthesis of oligosaccharides. Herein, a highly selective synthesis of β-mannosides and β-rhamnosides from glycosyl hemi-acetals is reported, following a one-pot chlorination,
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.
Copper-mediated anomeric: O -arylation with organoboron reagents
Dimakos, Victoria,Liu, Jacklyn J. W.,Ge, Zhenlu,Taylor, Mark S.
supporting information, p. 5671 - 5674 (2019/06/18)
Copper-mediated couplings of arylboroxines with glycosyl hemiacetals furnish O-aryl glycosides via Csp2-O bond formation. The method enables the anomeric O-arylation of protected pyranose and furanose derivatives, and is tolerant of functionalized arylboroxine partners. Whereas mixtures of anomers are formed from glucopyranose, galactopyranose and arabinofuranose hemiacetals, the α-anomer is generated selectively from mannopyranose and mannofuranose-derived substrates.
159. Glycosylidene Carbenes - Part 2 - Synthesis of O-Aryl Glycosides
Briner, Karin,Vasella, Andrea
, p. 1764 - 1779 (2007/10/02)
Phenol, 4-methoxyphenol, 4-nitrophenol, methyl orsellinate (1), and 2,6-di(tert-butyl)-4-methylphenol (BHT; 2) have been glycosylated by thermal reaction (20-60 deg C) with various glycosylidene-derived diazirines. 4-Methoxyphenol reacted with the D-gluco
