611182-25-3

Upstream product

• 476645-52-0 5-O-benzyl-3-deoxy-1,2-O-isopropylidene-3-C-p-tolylsulfanyl-α-D-xylofuranose 
• 476645-51-9 5-O-benzyl-1,2-O-isopropylidene-3-O-mesyl-α-D-ribofuranose 
• 34311-63-2 5-O-benzyl-3-oxo-1,2-O-isopropylidene-α-D-xylofuranose 
• 476645-53-1 methyl 5-O-benzyl-3-deoxy-3-C-p-tolylsulfanyl-α-D-xylofuranoside 

Downstream Products

• 476645-49-5 methyl 5-O-benzyl-2,3-dideoxy-3-C-(p)-tolylsulfonyl-α-D-erythro-pent-2-enofuranoside 

Relevant academic research and scientific papers

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.