476645-54-2

Upstream product

• 476645-51-9 5-O-benzyl-1,2-O-isopropylidene-3-O-mesyl-α-D-ribofuranose 
• 2592-42-9 5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose 
• 34311-63-2 5-O-benzyl-3-oxo-1,2-O-isopropylidene-α-D-xylofuranose 
• 20535-09-5 2,3-Anhydro-5-O-benzyl-β-D-ribofuranoside de methyle 
• 106-45-6 para-thiocresol 

Downstream Products

• 476645-50-8 methyl 5-O-benzyl-2,3-dideoxy-3-C-(p)-tolylsulfonyl-β-D-erythro-pent-2-enofuranoside 
• 1454318-66-1 (3R,4S,5R)-N-benzyl-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-amine 
• 1454318-57-0 (2R,3S,4R)-2-(benzyloxymethyl)-4-methoxy-3-((R)-p-tolylsulfinyl)-tetrahydrofuran 
• 1454318-46-7 (3S,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl methanesulfonate 
• 1454318-42-3 (3S,4R,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-ol 
• 1454318-64-9 dimethyl 2-((3R,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl)malonate 
• 1454318-65-0 (3R,4S,5R)-N-benzyl-5-(benzyloxymethyl)-4-((S)-p-tolylsulfinyl)-tetrahydrofuran-3-amine 
• 1454318-36-5 (2S,3R,4R)-5-(benzyloxy)-3-(p-tolylthio)pentane-1,2,4-triol 
• 1454318-63-8 dimethyl 2-((3R,4S,5R)-5-(benzyloxymethyl)-4-((S)-p-tosylsufinyl)-tetrahydrofuran-3-yl)malonate 
• 1454318-62-7 4-((3R,4S,5R)-5-(benzyloxymethyl)-4-tosyl-tetrahydrofuran-3-yl)morpholine 
• 1454318-61-6 (3R,4S,5R)-5-(benzyloxymethyl)-N-isopropyl-4-tosyl-tetrahydrofuran-3-amine 
• 1454318-60-5 (3R,4S,5R)-N-benzyl-5-(benzyloxymethyl)-4-tosyl-tetrahydrofuran-3-amine 
• 1454318-59-2 dimethyl 2-((3R,4S,5R)-5-(benzyloxymethyl)-4-tosyl-tetrahydrofuran-3-yl)malonate 
• 1454318-58-1 (2R,3S,4R)-2-(benzyloxymethyl)-4-(nitromethyl)-3-tosyl-tetrahydrofuran 

Relevant academic research and scientific papers

Vinyl sulfone- and vinyl sulfoxide-modified tetrahydrofurans: A preliminary account of the enantiomeric synthesis of and diastereoselectivity of addition to new classes of Michael acceptors

Enantiomerically pure 2-hydroxymethylene substituted-2,5-dihydro-3- (arylsulfonyl)- and 2-hydroxymethylene substituted-2,5-dihydro-3-(arylsulfinyl)- furans have been prepared from easily accessible carbohydrate derivatives for the first time. The strategy for accessing both these sulfones and sulfoxides is more efficient than the methods reported so far for the synthesis of this type of compounds. Hydroxymethylene group is sufficient to impose diastereoselectivity on the addition of a wide range of nucleophiles to vinyl sulfone-modified tetrahydrofurans. The benzyl protected hydroxymethylene group also suppresses the influence of chirally pure sulfoxides as two diastereomeric vinyl sulfoxide-modified tetrahydrofurans afforded the Michael adducts with same configurations at C-3 and C-4; this has been established by oxidizing the adducts, which were found to be identical to the products obtained by adding the same nucleophiles to the corresponding vinyl sulfones. These highly reactive Michael acceptors may be considered as a new addition to the arsenals of synthetic chemists interested in the functionalization of tetrahydrofurans.

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.

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.