1449009-45-3

Basic information

• Product Name: ((2S,3R,4R,5S,6R)-1-benzyl-3,4,5-tris(benzyloxy)-6-vinylpiperidin-2-yl)methanol
• Synonyms: ((2S,3R,4R,5S,6R)-1-benzyl-3,4,5-tris(benzyloxy)-6-vinylpiperidin-2-yl)methanol
• CAS NO: 1449009-45-3
• Molecular Weight: 549.71
• Mol File: 1449009-45-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ((2S,3R,4R,5S,6R)-1-benzyl-3,4,5-tris(benzyloxy)-6-vinylpiperidin-2-yl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: ((2S,3R,4R,5S,6R)-1-benzyl-3,4,5-tris(benzyloxy)-6-vinylpiperidin-2-yl)methanol(1449009-45-3)
• EPA Substance Registry System: ((2S,3R,4R,5S,6R)-1-benzyl-3,4,5-tris(benzyloxy)-6-vinylpiperidin-2-yl)methanol(1449009-45-3)

Safety Data

• Hazardous Substances Data: 1449009-45-3(Hazardous Substances Data)

Upstream product

• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 1449009-32-8 (3R,4R,5R,6S,7R)-1-benzyl-4,5,6-tris(benzyloxy)-7-vinylazepan-3-ol 
• 1354826-55-3 (1R,2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-8-oxa-6-azabicyclo[3.2.1]octane 
• 19139-89-0 (2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran 
• 114219-26-0 methyl 2,3,4-tri-O-benzyl-6-O-(4-methylbenzenesulfonyl)-α-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 

Relevant articles and documents

Skeletal rearrangement of seven-membered iminosugars: Synthesis of (-)-adenophorine, (-)-1-epi-adenophorine and derivatives and evaluation as glycosidase inhibitors

The mirror image of natural product (+)-adenophorine along with its 1-epi-, 1-homo-analogs and other derivatives have been synthesized and evaluated as glycosidase inhibitors. The synthetic strategy is based on the skeletal rearrangement of tetrahydroxylated C-alkyl azepanes obtained via a Staudinger/azaWittig/alkylation sequence starting from a sugar-derived azidolactol. Several organometallic species have been investigated for the alkylation step including organomagnesium, organolithium, organozinc, organoaluminum and organocerium reagents. While diallylzinc proved to be the most efficient to introduce an allyl substituent, disappointing results were obtained with the other organometallic species leading either to lower yields or no reaction. Enzymatic assays indicate that (-)-adenophorine is a moderate α-l-fucosidase inhibitor.