1040191-33-0

Basic information

• Product Name: N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide
• Synonyms: N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide
• CAS NO: 1040191-33-0
• Molecular Weight: 389.43
• Mol File: 1040191-33-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide(1040191-33-0)
• EPA Substance Registry System: N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide(1040191-33-0)

Safety Data

• Hazardous Substances Data: 1040191-33-0(Hazardous Substances Data)

Upstream product

• 7512-17-6 N-Acetyl-D-glucosamine 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 7512-17-6 2-acetamido-2-deoxy-D-glucose 
• 10036-64-3 N-acetyl-D-glucosamine 

Downstream Products

• 3946-01-8 methyl N-acetyl-β-D-glucosaminide 
• 6082-04-8 methyl 2-acetylamido-2-deoxy-D-glucoside 
• 147126-58-7 octyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside 
• 147126-57-6 octyl 2-N-acetyl-2-amino-2-deoxy-α-D-glucopyranoside 
• 54400-75-8 allyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 54400-75-8 allyl 2-acetamido-2-deoxy-α-D-glucopyranoside 
• 19124-40-4 isopropyl 2-acetamido-2-deoxy-α-D-glucopyranoside 
• 78341-33-0 isopropyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 3055-51-4 benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 13343-62-9 benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside 
• 21559-72-8 cyclohexyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside 
• 21559-73-9 cyclohexyl 2-(acetylamino)-2-deoxy-α-D-glucopyranoside 

Relevant articles and documents

Facile chemoenzymatic synthesis of Lewis a (Lea) antigen in gram-scale and sialyl Lewis a (sLea) antigens containing diverse sialic acid forms

An efficient streamlined chemoenzymatic approach has been developed for gram-scale synthesis of Lewis a angtigen (LeaβProN3) and a library of sialyl Lewis a antigens (sLeaβProN3) containing different sialic acid forms. Intially, commercially available inexpensive N-acetylglucosamine (GlcNAc) was converted to its N′-glycosyl p-toluenesulfonohydrazide in one step. Followed by chemical glycosylation, GlcNAcβProN3 was synthesized using this protecting group-free method in high yield (82%). Sequential one-pot multienzyme (OPME) β1–3-galactosylation of GlcNAcβProN3 followed by OPME α1–4-fucosylation reactions produced target LeaβProN3 in gram-scale. Structurally diverse sialic acid forms was successfully introduced using a OPME sialylation reation containing a CMP-sialic acid synthetase and Pasteurella multocida α2–3-sialyltransferase 1 (PmST1) mutant PmST1 M144D with or without a sialic acid aldolase to form sLeaβProN3 containing naturally occurring or non-natural sialic acid forms in preparative scales.

Protecting-group-free synthesis of glycosyl 1-phosphates

Glycosyl 1-phosphates enriched in the α-anomer are obtained without the use of protecting groups in two steps starting from the free hemiacetal. Condensation of free hemiacetals with toluenesulfonylhydrazide yields a range of glycosylsulfonohydrazide donors which can be oxidized using cupric chloride in the presence of phosphoric acid and the coordinating additive 2-methyl-2-oxazoline to give useful yields of the fully deprotected glycosyl 1-phosphates.

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.