157477-42-4

Upstream product

• 157363-85-4 1,2:5,6-Dianhydro-3,4-di-O-benzyl-D-mannitol 
• 100-46-9 benzylamine 
• 3396-11-0 cesium acetate 
• 176166-98-6 N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-2,6-di-O-methanesulfonyl-L-gulitol 
• 36199-02-7 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 

Downstream Products

• 176167-04-7 Benzoic acid (2S,3R,4R,5R)-1-benzyl-3,4-bis-benzyloxy-5-hydroxy-piperidin-2-ylmethyl ester 
• 157363-88-7 N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-L-gulitol 
• 172276-11-8 N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-L-iditol 
• 176166-99-7 N-benzyl-3,4-di-O-benzyl-2,5-dideoxy-2,5-imino-L-iditol 
• 176166-98-6 N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-2,6-di-O-methanesulfonyl-L-gulitol 
• 178964-40-4 1,6-dideoxy-1,6-imino-D-mannitol 

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.

Synthesis of azasugars. Part 2: Isomerization of polyhydroxylated azepanes

Isomerization of enantiopure C2-symmetric 3,5-dihydroxyazepane derivatives has been studied. The neighboring nitrogen participation occurs during mesylation to give a chloromethyl-piperidine, whereas from the L-ido-azepane a chiral bridged morp

Polyhydroxylated Piperidines and Azepanes from D-Mannitol. Synthesis of 1-Deoxynojirimycin and Analogues

D-mannitol and L-iditol bis-epoxides, easily obtained from D-mannitol, are convenient substrates for the synthesis of polyhydroxylated piperidines and azepanes, via a nucleophilic opening of one epoxy function followed by a spontaneous intramolecular ring closure.Using this strategy 1-deoxynojirimycin and analogues were prepared. - Key words: D-mannitol, Piperidine, Azepane, 1-deoxynojirimycin, 1,5-dideoxy-1,5-imino-L-gulitol, β-Glycosidase inhibitor.