231618-91-0

Upstream product

• 231618-87-4 (2S,3R,4R,5R)-N-butyloxycarbonyl-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidine-2-carbaldehyde 
• 173142-28-4 (1'R,2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>-2-<1',2'-dihydroxyethyl>pyrrolidine 
• 231619-09-3 (2R,3S,4S,5R,6R)-6-azido-2,3-epoxy-4,5,7-tris(benzyloxy)-2(E)-hepten-1-ol 
• 159063-89-5 (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidino<1,2-c>oxazole-3-one 
• 231618-88-5 (2R,3R,4R,5R)-N-butyloxycarbonyl-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>-2-(hydroxymethyl)pyrrolidine 
• 161290-43-3 (2R,3R,4R,5R)-2-(hydroxy-methyl)-3,4-di-O-benzyl-5-(O-benzyl-methyl)-pyrrolidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 845718-05-0 (2S,3R,4R,5R)-5-Azido-1,3,4-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-hexan-2-ol 
• 765308-78-9 1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-mannitol 
• 765308-79-0 1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-5-oxo-D-mannitol 
• 765308-80-3 (2R,3R,4R,5R)-2-(tert-butyl-dimethyl-sylanyloxy-methyl)-3,4-di-O-benzyl-5-(O-benzyl-methyl)-pyrrolidine 
• 765308-77-8 2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-mannitol 
• 231618-90-9 (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 231618-92-1 (2R,3R,4R,5R)-N-butyloxycarbonyl-2-(aminomethyl)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidine 
• 765308-82-5 (2R,3R,4R,5R)-2-(azido-methyl)-3,4-di-O-benzyl-5-(O-benzyl-methyl)-pyrrolidine 
• 231618-94-3 (2R,3R,4R,5R)-2-(acetamidomethyl)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidine 
• 231618-95-4 (2R,3R,4R,5R)-N-methyl-2-(acetamidomethyl)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidine 
• 231618-96-5 (2R,3R,4R,5R)-N-butyl-2-(acetamidomethyl)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidine 
• 231618-93-2 (2R,3R,4R,5R)-N-butyloxycarbonyl-2-(acetamidomethyl)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidine 

Relevant academic research and scientific papers

Synthesis and high-throughput screening of N-acetyl-β-hexosaminidase inhibitor libraries targeting osteoarthritis

C1 Nitrogen iminocyclitols are potent inhibitors of N-acetyl-β- hexosaminidases. Given hexosaminidases' important roles in osteoarthritis, we developed two straightforward and efficient syntheses of C1 nitrogen iminocyclitols from two readily available starting materials, D-mannosamine hydrochloride and the microbial oxidation product of fructose. A diversity-oriented synthetic strategy was then performed by coupling these core structures with various aldehydes, carboxylic acids, and alkynes to generate three separate libraries. High-throughput screening of the generated libraries with human N-acetyl-β-hexosaminidases produced only moderate inhibitory activities. However, the synthetic approach and screening strategy for these compounds will be applied to develop new potent inhibitors of human N-acetyl-β-hexosaminidases, particularly when combined with the structural information of these enzymes.

Iminocyclitol inhibitors of hexoaminidase and glycosidase

Designed iminocylitols that have potent inhibition activity with respect to hexominidases and glycosides are disclosed.

A versatile synthetic strategy for the preparation and discovery of new iminocyclitols as inhibitors of glycosidases

A series of iminocyclitols was prepared using a versatile synthetic strategy, and their inhibition of glycosidases was evaluated using capillary electrophoresis. The study has demonstrated that remarkable specificities in enzyme inhibition can be achieved with small modifications on the aglycon side chain and the ring nitrogen. Among the compounds synthesized, (2R,3R,4R,5R)-N-methyl-2(acetamidomethyl)-3,4-dihydroxy-5- (hydroxymethyl)pyrrolidine was found to be very potent against β-N- acetylhexosaminidase P with the K(i) value of 80 nM.