78341-33-0

Usage

Uses

Used in Chemical Synthesis Industry:
ISO-PROPYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE is used as a glycosyl acceptor for the chemical synthesis of N-acetylglucosamine derivatives. This is achieved through the action of the Mesorhizobium loti chitin oligosaccharide synthase NodC enzyme, which plays a crucial role in the biosynthesis of chitin oligosaccharides.

Upstream product

• 72-87-7 2-Acetylamino-2-desoxy-DL-glucopyranose 
• 13264-92-1 o-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 67-63-0 isopropyl alcohol 
• 117177-19-2 2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline 
• 13089-26-4 o-nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 1040191-33-0 N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide 
• 7512-17-6 N-Acetyl-D-glucosamine 

Relevant academic research and scientific papers

Chemo-enzymatic approach to access diastereopure α-substituted GlcNAc derivatives

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

(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

(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.

The use of the o-nitrophenyl group as a protecting/activating group for 2-acetamido-2-deoxyglucose

The o-nitrophenyl group, a protecting group with latent activation potential, was used as a protecting group for the glycosidic position. It is stable to common conditions used in synthesis and can be activated for displacement and glycoside formation by an alcohol, using zinc chloride as a catalyst. Good to excellent yields of β-glycosides of the important amino sugar N-acetylglucosamine were obtained. A mechanism for the reaction is proposed.