19124-40-4Relevant academic research and scientific papers
Chemo-enzymatic approach to access diastereopure α-substituted GlcNAc derivatives
Wang, Su-Yan,Laborda, Pedro,Lu, Ai-Min,Wang, Meng,Duan, Xu-Chu,Liu, Li,Voglmeir, Josef
, p. 423 - 434 (2016)
The formation of diastereopure α-substituted GlcNAc derivatives in a simple and straightforward way is a challenging task. Herein, we report the chemical synthesis of diastereomeric α/β-substituted GlcNAc derivatives under non-anhydrous atmosphere using u
Protecting group free glycosidations using p-toluenesulfonohydrazide donors
Gudmundsdottir, Anna V.,Nitz, Mark
supporting information; scheme or table, p. 3461 - 3463 (2009/04/16)
(Figure Presented) N-Glycopyranosylsulfonohydrazides are introduced as glycosyl donors for protecting group free synthesis of O-glycosides, glycosyl azides, and oxazolines. Mono- and disaccharides containing a reducing terminal N-acelylglucosamine residue were condensed with p-toluenesulfonylhydrazide to give the desired β-D-pyranose donors. These donors can be activated with NBS and then glycosidated with the desired alcohol or transformed to the oxazoline or glycosyl azide.
Facile approach to 2-acetamido-2-deoxy-β-D-glucopyranosides via a furanosyl oxazoline
Cai, Ye,Ling, Chang-Chun,Bundle, David R.
, p. 4021 - 4024 (2007/10/03)
(Chemical Equation Presented) A concise and convenient route that may be easily scaled is reported for the preparation of unprotected β-glucopyranosides of N-acetyl-D-glucosamine. Reaction of a wide variety of alcohols with a reactive, readily prepared furanosyl oxazoline under acidic conditions affords the corresponding β-D-glucopyranosides in good to high yields. Primary alcohols gave only β-D-glucopyranosides. A mechanism is proposed for this transformation.
