Chang, Chun-Wei; Wu, Chia-Hui; Lin, Mei-Huei; Liao, Pin-Hsuan; Chang, Chun-Chi; Chuang, Hsiao-Han; Lin, Su-Ching; Lam, Sarah; Verma, Ved Prakash; Hsu, Chao-Ping; Wang, Cheng-Chung published the artcile< Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity>, SDS of cas: 128-09-6, the main research area is predicted stereocontrolled glycosylation relative reactivity thioglycoside; carbohydrates; diastereoselectivity; glycosylation.
Stereocontrolled chem. glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.
Angewandte Chemie, International Edition published new progress about Diastereoselective synthesis. 128-09-6 belongs to class chlorides-buliding-blocks, and the molecular formula is C4H4ClNO2, SDS of cas: 128-09-6.
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics