139189-57-4

Basic information

• Product Name: 2,3,4,6-tetra-O-benzyl-D-glucononitrile
• Synonyms: 2,3,4,6-tetra-O-benzyl-D-glucononitrile
• CAS NO: 139189-57-4
• Molecular Weight: 537.656
• Mol File: 139189-57-4.mol

Chemical Properties

• CAS DataBase Reference: 2,3,4,6-tetra-O-benzyl-D-glucononitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-tetra-O-benzyl-D-glucononitrile(139189-57-4)
• EPA Substance Registry System: 2,3,4,6-tetra-O-benzyl-D-glucononitrile(139189-57-4)

Safety Data

• Hazardous Substances Data: 139189-57-4(Hazardous Substances Data)

Upstream product

• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 86496-30-2 (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexanal oxime 
• 139189-61-0 2,3,4,6-tetra-O-benzyl-D-xylo-hex-5-ulosononitrile 

Downstream Products

• 139189-62-1 2,3,4,6-tetra-O-benzyl-L-idononitrile 
• 139189-63-2 2,3,4,6-tetra-O-benzyl-5-O-(4-toluenesulfonyl)-L-idononitrile 
• 139189-64-3 (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine 
• 69567-11-9 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 52492-43-0 2,3,5-tri-O-benzyl-β-D-arabinofuranosyl cyanide 
• 4132-27-8 1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranose 
• 139189-61-0 2,3,4,6-tetra-O-benzyl-D-xylo-hex-5-ulosononitrile 
• 139189-59-6 2,3,4,6-tetra-O-benzyl-5-deoxy-5-iodo-L-idononitrile 
• 139189-60-9 2,5-anhydro-3,4,6-tri-O-benzyl-L-idononitrile 
• 139189-58-5 2,3,4,6-tetra-O-benzyl-5-bromo-5-deoxy-L-idononitrile 

Relevant articles and documents

Sugar hydrazide imides: A new family of glycosidase inhibitors

The preparation of a novel type of iminosugar including a hydrazide imide moiety is described. The sugar hydrazide imides (3S,4S,5R,6R)-1-amino-3,4,5-trihydroxy-6-(hydroxymethyl)-2-iminopiperidine acetate and (3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethy

One pot oxidative dehydration - oxidation of polyhydroxyhexanal oxime to polyhydroxy oxohexanenitrile: A versatile methodology for the facile access of azasugar alkaloids

A unique oxidative dehydration-oxidation of polyhydroxy-oxime (7) to the corresponding ketonitrile (8) in one pot is reported for the first time in carbohydrate literature. Key ketonitrile intermediate (8) upon palladium hydroxide mediated cascade reaction afforded 1-deoxynojirimycin (DNJ) 1b in moderate diastereoselectivity. The cascade reaction involves the conversion of nitrile to amine, heteroannulation, reduction of the imine and subsequent debenzylation to furnish the azasugars. This oxidative dehydration-oxidation and reductive heteroannulation methodology is successfully utilized for the total synthesis of 1-deoxynojirimycin (1b), miglitol (2) and miglustat (3).