176166-99-7

Upstream product

• 176166-98-6 N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-2,6-di-O-methanesulfonyl-L-gulitol 
• 3396-11-0 cesium acetate 
• 36199-02-7 3,4-di-O-benzyl-D-mannitol 
• 157363-85-4 1,2:5,6-Dianhydro-3,4-di-O-benzyl-D-mannitol 
• 157363-88-7 N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-L-gulitol 
• 157477-42-4 N-benzyl-3,4-di-O-benzyl-1,6-dideoxy-1,6-imino-D-mannitol 

Downstream Products

• 105015-44-9 (2S,3R,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)pyrrolidine 

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.