76670-94-5

Basic information

• Product Name: 2,3,4,6-tetra-O-benzyl-5-dehydro-5-oxo-D-gluconamide
• Synonyms: 2,3,4,6-tetra-O-benzyl-5-dehydro-5-oxo-D-gluconamide
• CAS NO: 76670-94-5
• Molecular Weight: 553.655
• Mol File: 76670-94-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2,3,4,6-tetra-O-benzyl-5-dehydro-5-oxo-D-gluconamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-tetra-O-benzyl-5-dehydro-5-oxo-D-gluconamide(76670-94-5)
• EPA Substance Registry System: 2,3,4,6-tetra-O-benzyl-5-dehydro-5-oxo-D-gluconamide(76670-94-5)

Safety Data

• Hazardous Substances Data: 76670-94-5(Hazardous Substances Data)

Upstream product

• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 76670-93-4 2,3,4,6-tetra-O-benzyl-D-gluconamide 

Downstream Products

• 227932-82-3 N-butyl 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 72599-27-0 N-butyldeoxynojirimycin 
• 77174-08-4 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one 
• 263720-36-1 (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(2-phenylethynyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine 
• 263719-95-5 (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2,3-diiodo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine 
• 244138-64-5 (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-iodo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine 
• 191863-33-9 (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)-methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine 
• 153996-70-4 2,3,4,6-tetra-O-benzyl-D-glucono-δ-thiolactam 
• 1300698-48-9 2,2-dimethyl-N-phenyl-4-((5R,6R,7S,8S)-6,7,8-trihydroxy-5-(hydroxymethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)but-3-ynamide 
• 1300698-47-8 N-phenyl-3-((5R,6R,7S,8S)-6,7,8-trihydroxy-5-(hydroxymethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)propanamide 
• 1300698-46-7 (5R,6R,7S,8S)-2-(4-fluorophenethyl)-5-(hydroxymethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol 
• 1300698-45-6 (5R,6R,7S,8S)-2-(4-cyclohexylphenethyl)-5-(hydroxymethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol 
• 1300698-44-5 (5R,6R,7S,8S)-2-(2-(biphenyl-4-yl)ethyl)-5-(hydroxymethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol 
• 1300698-43-4 (5R,6R,7S,8S)-5-(hydroxymethyl)-2-(4-methoxyphenethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol 

Relevant articles and documents

Synthesis of 1-deoxynojirimycin: Exploration of optimised conditions for reductive amidation and separation of epimers

1-Deoxynojirimycin (DNJ), which has importance with respect to sugar processing enzymes, is a synthetic target for chemists. A key step in the synthesis of DNJ is the preparation of 2,3,4,6-tetra-O-benzyl-D-glucono-δ-lactam. By varying reaction parameters such as temperature, solvent and reducing reagent, improvements on previous methods are described. A novel approach for the synthesis of 2,3,4,6-tetra-O-benzyl-5-dehydro-5-deoxo-D-gluconamide has been developed by using PCC as an oxidising agent. Separation of epimers permitted DNJ to be obtained in 85% yield after reduction and hydrogenolysis steps.

Structure-activity relationships in a series of C2-substituted gluco-configured tetrahydroimidazopyridines as β-glucosidase inhibitors

Inhibition of glycoside hydrolases has widespread application in treatment of diabetes, viral infections, lysosomal storage diseases and cancers. Gluco-configured tetrahydroimidazopyridines are the most potent β-glucosidase inhibitors reported to date. Using transition state mimic strategy, a series of C2-substituted gluco-configured tetrahydroimidazopyridines were designed and synthesized. Compounds 3 (Ki = 0.64 nM) and 5 (Ki = 0.58 nM) showed stronger inhibitory potency against β-glucosidase. Maestro 9.1 was used to study the structure-activity relationships by docking the compounds into the β-glucosidase active sites. Crown Copyright

A Facile Transformation of Sugar Lactones to Azasugars

The synthesis of pyrano- and furano- sugar lactams from the corresponding lactones, in a five step sequence, is described.