157363-86-5

Basic information

• Product Name: N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol
• Synonyms: N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol
• CAS NO: 157363-86-5
• Molecular Weight: 433.547
• Mol File: 157363-86-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol(157363-86-5)
• EPA Substance Registry System: N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol(157363-86-5)

Safety Data

• Hazardous Substances Data: 157363-86-5(Hazardous Substances Data)

Upstream product

• 157363-84-3 1,2:5,6-dianhydro-3,4-di-O-benzyl-L-iditol 
• 100-46-9 benzylamine 
• 176300-11-1 N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-2,6-di-O-methanesulfonyl-D-glucitol 
• 172147-86-3 Methanesulfonic acid (1R,2S,3S,4R)-2,3-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-methanesulfonyloxy-pentyl ester 
• 172147-87-4 (2R,3R,4R,5R)-3,4-Bis-benzyloxy-1,6-bis-(tert-butyl-dimethyl-silanyloxy)-hexane-2,5-diol 
• 36199-02-7 3,4-di-O-benzyl-D-mannitol 
• 189267-11-6 N-benzyl-2,6-di-O-benzoyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 189267-09-2 2,6-di-O-acetyl-N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 

Downstream Products

• 189267-13-8 1,6-di-O-acetyl-N-benzyl-3,4-di-O-benzyl-2,5-dideoxy-2,5-imino-D-mannitol 
• 189267-09-2 2,6-di-O-acetyl-N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 189267-36-5 (2S,3R,4R,5S)-3,4-Bis-benzyloxy-5-hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 
• 189267-29-6 (6R,7R,8R,8aR)-6-Azido-7,8-bis-benzyloxy-hexahydro-oxazolo[3,4-a]pyridin-3-one 
• 189267-32-1 2-azido-3,4-di-O-benzyl-1,2,5-trideoxy-1,5-imino-D-mannitol 
• 189267-26-3 (6S,7R,8R,8aR)-7,8-Bis-benzyloxy-6-hydroxy-hexahydro-oxazolo[3,4-a]pyridin-3-one 
• 176167-00-3 N-benzyloxycarbonyl-3,4-di-O-benzyl-2,6-di-O-benzoyl-1,5-dideoxy-1,5-imino-D-mannitol 
• 176483-87-7 N-benzyloxycarbonyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 59920-31-9 2,5-dideoxy-2,5-imino-D-mannitol 
• 94119-08-1 3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-mannitol 
• 14199-63-4 1-deoxymannojirimycin 
• 189267-11-6 N-benzyl-2,6-di-O-benzoyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 189267-16-1 N-benzyl-1,6-di-O-benzoyl-3,4-di-O-benzyl-2,5-dideoxy-2,5-imino-D-mannitol 
• 176300-12-2 N-benzyl-3,4-di-O-benzyl-2,5-dideoxy-2,5-imino-D-mannitol 

Relevant articles and documents

Syntheses and evaluation as glycosidase inhibitor of 1,5-dideoxy-1,5-imino-D-glucitol analogs of salacinol, a potent α-glucosidase inhibitor isolated from ayurvedic medicine, Salacia reticulata

N-Alkylated deoxynojirimycin (10) bearing the same alkyl chain as salacinol (1), a potent α-glucosidase inhibitor isolated from Ayurvedic traditional medicine, Salacia reticulata, was found to inhibit both rat intestinal maltase and sucrase as strong as 1, while 10 has been reported to be inactive against glucoamylase G2 from Aspergillus niger. Its O-desulfate (12) was also found active against these enzymes, and characteristic sulfate anion moiety of 1 was found not essential for the α-glucosidase inhibitory activity.

Synthesis of azasugars. Part 1. Isomerization of polyhydroxylated piperidines

N-Benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol and L-gulitol undergo easy isomerization, mainly either by ring contraction, or either by SN2 inversion at C2. This isomerization performed by bis-hydroxyl activation allows to access to 2,5-dideoxy-2,5-imino-L-iditol, 5-epi-DNJ, DMDP, and DMJ.