176483-87-7

Upstream product

• 501-53-1 benzyl chloroformate 
• 189267-23-0 3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 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 
• 176300-11-1 N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-2,6-di-O-methanesulfonyl-D-glucitol 
• 157363-86-5 N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 157363-84-3 1,2:5,6-dianhydro-3,4-di-O-benzyl-L-iditol 
• 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 

Downstream Products

• 176167-00-3 N-benzyloxycarbonyl-3,4-di-O-benzyl-2,6-di-O-benzoyl-1,5-dideoxy-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 
• 189267-36-5 (2S,3R,4R,5S)-3,4-Bis-benzyloxy-5-hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 
• 14199-63-4 1-deoxymannojirimycin 
• 94119-08-1 3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-mannitol 
• 189267-32-1 2-azido-3,4-di-O-benzyl-1,2,5-trideoxy-1,5-imino-D-mannitol 
• 189267-29-6 (6R,7R,8R,8aR)-6-Azido-7,8-bis-benzyloxy-hexahydro-oxazolo[3,4-a]pyridin-3-one 

Relevant academic research and scientific papers

Synthesis of azasugars as potent inhibitors of glycosidases

A series of enantiomerically pure azasugars (2,5-dideoxy-2,5-imino-D-mannitol, 1-deoxynojirimycin, 1-deoxymannojirimycin, and related compounds) was synthesized from D-mannitol via aminoheterocyclization of C2-symmetric bis-epoxides and subsequently followed by ring isomerization in few cases. These compounds have been evaluated as inhibitors of several glycosidases (α- and β-D-glucosidases, α-D-mannosidase and α-L-fucosidase). Inhibition studies indicate notably that the polyhydroxylated azepanes are inhibitors of glycosidases, with K(i) in the micromolar range.

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.