94119-08-1

Upstream product

• 176167-00-3 N-benzyloxycarbonyl-3,4-di-O-benzyl-2,6-di-O-benzoyl-1,5-dideoxy-1,5-imino-D-mannitol 
• 157363-86-5 N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 94152-35-9 Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-methoxy-6-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-3-yl ester 
• 76419-48-2 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 
• 591727-19-4 1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 
• 57783-73-0 methyl 3,4-di-O-benzyl-α-D-glucopyranoside 
• 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 
• 501-53-1 benzyl chloroformate 
• 94119-07-0 (1R,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-methoxy-2-oxa-5-aza-bicyclo[2.2.2]octane-5-carboxylic acid benzyl ester 
• 94160-77-7 methyl 2-O-trifluoromethanesulfonyl-3-O-benzyl-(R)-4,6-O-benzylidene-α-D-glucopyranoside 
• 94119-05-8 Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-6-aminomethyl-4,5-bis-benzyloxy-2-methoxy-tetrahydro-pyran-3-yl ester 
• 94160-78-8 methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside 

Downstream Products

• 14199-63-4 1-deoxymannojirimycin 

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.

SYNTHESES OF 1,5-DIDEOXY-1,5-IMINO-D-MANNITOL FROM D-MANNOSE AND D-GLUCOSE

Unambigous enantiospecific syntheses of 1,5-dideoxy-1,5-imino-D-mannitol (LU1, 1-deoxy-mannojirimycin) are reported (i) from D-mannose via hydrogenation of a 5-azido-5-deoxy mannose, and (ii) from D-glucose, in which the key step involves nucleophilic substitution of a trifluoromethanesulphonyl group from C-2 of D-glucose.