476645-51-9

Basic information

• Product Name: 5-O-benzyl-1,2-O-isopropylidene-3-O-mesyl-α-D-ribofuranose
• Synonyms: 5-O-benzyl-1,2-O-isopropylidene-3-O-mesyl-α-D-ribofuranose
• CAS NO: 476645-51-9
• Molecular Weight: 358.412
• Mol File: 476645-51-9.mol

Chemical Properties

• CAS DataBase Reference: 5-O-benzyl-1,2-O-isopropylidene-3-O-mesyl-α-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 5-O-benzyl-1,2-O-isopropylidene-3-O-mesyl-α-D-ribofuranose(476645-51-9)
• EPA Substance Registry System: 5-O-benzyl-1,2-O-isopropylidene-3-O-mesyl-α-D-ribofuranose(476645-51-9)

Safety Data

• Hazardous Substances Data: 476645-51-9(Hazardous Substances Data)

Upstream product

• 2592-42-9 5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose 
• 124-63-0 methanesulfonyl chloride 
• 34311-63-2 5-O-benzyl-3-oxo-1,2-O-isopropylidene-α-D-xylofuranose 

Downstream Products

• 611182-25-3 methyl 5-O-benzyl-3-deoxy-3-C-p-tolylsulfonyl-α-D-xylofuranoside 
• 611182-23-1 methyl 5-O-benzyl-3-deoxy-3-C-p-tolylsulfonyl-β-D-xylofuranoside 
• 476645-53-1 methyl 5-O-benzyl-3-deoxy-3-C-p-tolylsulfanyl-α-D-xylofuranoside 
• 476645-54-2 methyl 5-O-benzyl-3-deoxy-3-C-p-tolylsulfanyl-β-D-xylofuranoside 
• 476645-49-5 methyl 5-O-benzyl-2,3-dideoxy-3-C-(p)-tolylsulfonyl-α-D-erythro-pent-2-enofuranoside 
• 476645-50-8 methyl 5-O-benzyl-2,3-dideoxy-3-C-(p)-tolylsulfonyl-β-D-erythro-pent-2-enofuranoside 
• 476645-52-0 5-O-benzyl-3-deoxy-1,2-O-isopropylidene-3-C-p-tolylsulfanyl-α-D-xylofuranose 

Relevant articles and documents

A glycosylation driven strategy for the synthesis of anomerically pure vinyl sulfone-modified pent-2-enofuranoses and hex-2-enopyranoses

Both α- and β-anomers of vinyl sulfone-modified pent-2-enofuranosides have been synthesized for the first time by taking advantage of the formation of α- and β-methyl glycosides in almost equal ratio only from derivatives of D-xylose. The strategy was equally applicable in the synthesis of α- and β-anomers of vinyl sulfone-modified hex-2-enopyranosides where a D-glucose derivative was selected over a D-allose derivative as the starting material because the former almost exclusively produced the required methyl pyranosides.

Synthesis of anomerically pure vinyl sulfone-modified pent-2-enofuranosides and hex-2-enopyranosides: A group of highly reactive Michael acceptors for accessing carbohydrate based synthons

Syntheses of the benzyl or the trityl protected α- and β-anomers of vinyl sulfone-modified pent-2-enofuranosides have been initiated by the ring opening of the suitably masked methyl α-lyxofuranosyl-epoxide or methyl β-ribofuranosyl-epoxide or by the nucleophilic displacement of the leaving groups in benzyl protected 3-O-tosyl xylofuranoside and 3-O-mesyl ribofuranoside by p-thiocresol. In case of the latter set of starting materials, α- and β-methyl glycosides formed in almost equal ratio only from the derivatives of D-xylose. For the synthesis of α- and β-anomers of vinyl sulfone-modified hex-2-enopyranosides, a D-glucose derivative was selected over a D-allose derivative as the starting material because the former almost exclusively produced the required methyl pyranosides whereas the latter produced a mixture. All sulfides were converted to vinyl sulfone-modified carbohydrates by the sequential application of oxidation, mesylation and base induced elimination reactions.