611182-18-4

Basic information

• Product Name: methyl 5-O-benzyl-3-deoxy-3-C-p-tolylsulfanyl-α-D-arabinofuranoside
• Synonyms: methyl 5-O-benzyl-3-deoxy-3-C-p-tolylsulfanyl-α-D-arabinofuranoside
• CAS NO: 611182-18-4
• Molecular Weight: 360.474
• Mol File: 611182-18-4.mol

Chemical Properties

• CAS DataBase Reference: methyl 5-O-benzyl-3-deoxy-3-C-p-tolylsulfanyl-α-D-arabinofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 5-O-benzyl-3-deoxy-3-C-p-tolylsulfanyl-α-D-arabinofuranoside(611182-18-4)
• EPA Substance Registry System: methyl 5-O-benzyl-3-deoxy-3-C-p-tolylsulfanyl-α-D-arabinofuranoside(611182-18-4)

Safety Data

• Hazardous Substances Data: 611182-18-4(Hazardous Substances Data)

Upstream product

• 14645-49-9 methyl 2,3-anhydro-5-O-benzyl-α-D-lyxofuranoside 
• 106-45-6 para-thiocresol 

Downstream Products

• 476645-49-5 methyl 5-O-benzyl-2,3-dideoxy-3-C-(p)-tolylsulfonyl-α-D-erythro-pent-2-enofuranoside 
• 1407485-26-0 C₂₀H₂₂O₄S 
• 1407485-24-8 C₂₀H₂₂O₄S 
• 1407485-25-9 C₂₁H₂₆O₇S₂ 
• 1407485-27-1 C₂₁H₂₆O₇S₂ 
• 1407485-23-7 C₂₀H₂₄O₅S 
• 1407485-22-6 C₂₀H₂₄O₅S 
• 1407485-34-0 C₂₁H₂₅NO₆S 
• 1407485-35-1 C₂₁H₂₅NO₆S 
• 611182-21-9 methyl 5-O-benzyl-3-deoxy-3-C-p-tolylsulfonyl-α-D-arabinofuranoside 

Relevant articles and documents

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.