478175-66-5

Basic information

• Product Name: benzyl 2,3-O-isopropylidene-β-L-xylopyranoside
• Synonyms: benzyl 2,3-O-isopropylidene-β-L-xylopyranoside
• CAS NO: 478175-66-5
• Molecular Weight: 280.321
• Mol File: 478175-66-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: benzyl 2,3-O-isopropylidene-β-L-xylopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 2,3-O-isopropylidene-β-L-xylopyranoside(478175-66-5)
• EPA Substance Registry System: benzyl 2,3-O-isopropylidene-β-L-xylopyranoside(478175-66-5)

Safety Data

• Hazardous Substances Data: 478175-66-5(Hazardous Substances Data)

Upstream product

• 116-11-0 2-Methoxypropene 
• 478175-99-4 benzyl β-L-xylopyranoside 
• 869848-87-3 tri-O-acetyl-L-xylopyranosyl trichloroacetimidate 
• 100-51-6 benzyl alcohol 

Downstream Products

• 478175-68-7 benzyl 2,3-O-isopropylidene-4-O-(N-phthalimido)-α-D-arabinoside 
• 770735-90-5 benzyl 4-C-cyano-4-deoxy-α-D-arabinoside 
• 958001-17-7 benzyl 4-[N-amino-N-(tert-butoxycarbonyl)]amino-4-deoxy-2,3-O-isopropylidene-α-D-arabinopyranoside 
• 958001-15-5 benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-2-O-isopropyl-α-D-arabinopyranoside 
• 958001-26-8 benzyl 4-[N-tert-butoxycarbonyl-N-(tert-butoxycarbonyl)-amino]amino-4-deoxy-α-D-arabinopyranoside 
• 958001-21-3 benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-2,3-bis-O-(trimethylsilyl)-α-D-arabinopyranoside 
• 958001-24-6 benzyl 4-[N-tert-butoxycarbonyl-N-di(tert-butoxycarbonyl)-amino]amino-4-deoxy-2,3-O-isopropylidene-α-D-arabinopyranoside 
• 958001-25-7 benzyl 4-[N-tert-butoxycarbonyl-N-di(tert-butoxycarbonyl)-amino]amino-4-deoxy-α-D-arabinopyranoside 
• 958001-19-9 benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-2,3-di-O-(tert-butyldimethylsilyl)-4-deoxy-α-D-arabinopyranoside 
• 226988-19-8 (-)-(3S,4S,5S)-4,5-dihydroxy-3-hydroxymethylhexahydropyridazine 
• 478175-78-9 benzyl 4-cyano-4-deoxy-2,3-O-isopropylidene-α-D-arabinoside 
• 478175-82-5 benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-α-D-arabinopyranoside 
• 478175-80-3 benzyl 4-{[(tert-butoxycarbonyl)amino]methyl}-4-deoxy-2,3-O-isopropylidene-α-D-arabinoside 
• 478175-72-3 benzyl 4-O-[(tert-butoxycarbonyl)amino]-α-D-arabinoside 

Relevant articles and documents

The synthesis of a carbohydrate-like dihydrooxazine and tetrahydrooxazine as putative inhibitors of glycoside hydrolases: A direct synthesis of isofagomine

The treatment of benzyl 2,3-O-isopropylidene-β-L-xylopyranoside with N-hydroxyphthalimide under Mitsunobu conditions, followed by protecting-group interchange, gave benzyl 4-O-[(tert-butoxycarbonyl)amino]-2,3-O-isopropylidene-α-D-arabinoside. Mild acid hydrolysis and catalytic hydrogenolysis afforded 4-O-[(tert-butoxycarbonyl)amino]-D-arabinose that, upon heating in water, gave the dihydrooxazine [(4R,5S,6R)-5,6-dihydro-4,5-dihydroxy-6-hydroxymethyl-4H-1,2-oxazine] as a crystalline solid. A single-crystal structure determination of this solid showed it to exist in the 5H6 conformation. Reduction of the dihydrooxazine gave the tetrahydrooxazine [(4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-3,4,5,6-tetrahydro-2H-1,2-oxazine]. The dihydrooxazine was an effective inhibitor of two β-glucosidases (Ki = 27 and 35 μM). Benzyl 2,3-O-isopropylidene-β-L-xylopyranoside, via the derived imidazylate, was converted into a nitrile that, upon reduction and protecting-group manipulations, gave benzyl 4-C-aminomethyl-4-deoxy-α-D-arabinoside. Treatment of this amine with hydrogen and palladium-on-carbon gave isofagomine.