147126-58-7Relevant articles and documents
Straightforward glycosylation of alcohols and amino acids mediated by ionic liquid
Monasson, Olivier,Sizun-Thomé, Gwena?lle,Lubin-Germain, Nadège,Uziel, Jacques,Augé, Jacques
scheme or table, p. 202 - 205 (2012/06/30)
Green glycosylation of functionalized alcohols and α-amino acids, using an ionic liquid as a recyclable solvent, was performed in one step directly from the unprotected monosaccharide under scandium triflate or ferric chloride catalysis. Pure α- and β-glycosides could be obtained after specific enzymatic hydrolysis.
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.
