94119-08-1

Basic information

• Product Name: 3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-mannitol
• Synonyms: 3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-mannitol
• CAS NO: 94119-08-1
• Molecular Weight: 477.557
• Mol File: 94119-08-1.mol

Chemical Properties

• CAS DataBase Reference: 3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-mannitol(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-mannitol(94119-08-1)
• EPA Substance Registry System: 3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-mannitol(94119-08-1)

Safety Data

• Hazardous Substances Data: 94119-08-1(Hazardous Substances Data)

Upstream product

• 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 
• 176167-00-3 N-benzyloxycarbonyl-3,4-di-O-benzyl-2,6-di-O-benzoyl-1,5-dideoxy-1,5-imino-D-mannitol 
• 501-53-1 benzyl chloroformate 
• 172147-87-4 (2R,3R,4R,5R)-3,4-Bis-benzyloxy-1,6-bis-(tert-butyl-dimethyl-silanyloxy)-hexane-2,5-diol 
• 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 
• 157363-84-3 1,2:5,6-dianhydro-3,4-di-O-benzyl-L-iditol 
• 157363-86-5 N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 189267-23-0 3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 176483-87-7 N-benzyloxycarbonyl-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 
• 189267-09-2 2,6-di-O-acetyl-N-benzyl-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 
• 57783-73-0 methyl 3,4-di-O-benzyl-α-D-glucopyranoside 
• 94119-06-9 (1R,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-methoxy-2-oxa-5-aza-bicyclo[2.2.2]octane 

Downstream Products

• 14199-63-4 1-deoxymannojirimycin 

Relevant articles and documents

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.