196093-24-0

Basic information

• Product Name: 5-O-benzoyl-4-O-methanesulfonyl-2,3-O-isopropylidene-L-arabinose diethyl dithioacetal
• Synonyms: 5-O-benzoyl-4-O-methanesulfonyl-2,3-O-isopropylidene-L-arabinose diethyl dithioacetal
• CAS NO: 196093-24-0
• Molecular Weight: 478.652
• Mol File: 196093-24-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-O-benzoyl-4-O-methanesulfonyl-2,3-O-isopropylidene-L-arabinose diethyl dithioacetal(CAS DataBase Reference)
• NIST Chemistry Reference: 5-O-benzoyl-4-O-methanesulfonyl-2,3-O-isopropylidene-L-arabinose diethyl dithioacetal(196093-24-0)
• EPA Substance Registry System: 5-O-benzoyl-4-O-methanesulfonyl-2,3-O-isopropylidene-L-arabinose diethyl dithioacetal(196093-24-0)

Safety Data

• Hazardous Substances Data: 196093-24-0(Hazardous Substances Data)

Upstream product

• 92936-93-1 (4R,5S)-4-(bis(ethylthio)methyl)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-1,3-dioxolane 
• 43179-48-2 L-arabinose di(ethylthio)acetal 
• 532-32-1 sodium benzoate 
• 196093-23-9 4,5-di-O-methanesulfonyl-2,3-O-isopropylidene-L-arabinose diethyl dithioacetal 

Downstream Products

• 196093-30-8 Thiobenzoic acid S-{(S)-2-azido-2-[(4S,5R)-5-(bis-ethylsulfanyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl} ester 
• 196093-34-2 4-azido-5-S-benzoyl-4-deoxy-2,3-O-isopropylidene-5-thio-D-xylose 
• 91876-82-3 4-azido-5-O-benzoyl-4-deoxy-2,3-O-isopropylidene-D-xylose diethyl dithioacetal 

Relevant articles and documents

Synthesis of 4-cyanophenyl 4-azido-4-deoxy-1,5-dithio-β-D-xylopyranoside

L-Arabinose diethyl dithioacetal was converted, via its 4-azido-5-S-benzoyl-4-deoxy-2,3-O-isopropylidene-5-thio-D-xylose diethyl dithioacetal, into 4-azido-4-deoxy-5-thio-α-D-xylopyranose triacetate 29. Glycosidation of 29 with 4-cyanothiophenol in the presence of trimethylsilyl triflate gave the 4-cyanophenyl 2,3-di-O-acetyl-4-azido-4-deoxy-1,2-dithio-α- and -β-D-xylopyranosides 31 and 33 as well as 3-O-acetyl-2,5-anhydro-4-azido-4-deoxy-5- thio-D-lyxose bis(4-cyanophenyl) dithioacetal 34 in a 8:2:1 respective ratio. Treatment of 29 with hydrogen bromide in acetic acid yielded a 1:4 mixture of 2,3-di-O-acetyl-4-azido-4-deoxy-5-thio-D-xylopyranosyl bromide 38 and 2,3 -di-O-acetyl-5-bromo-5-deoxy-4-thio-L-arabinofuranosyl bromide 40. Reaction of the mixture of bromides 38 and 40 with 4-cyanothiophenol in the presence of potassium carbonate afforded the expected 31 and 33 only in traces, while 2-(1R,2S,-1,2-di-O-acetyl-1,2-dihydroxy-but-3-en-1-yl)-5-cyano-1,3 dithiole and 4-cyanophenyl 2,3-di-O-acetyl-5-S-(4-cyanophenyl)-1,4,5-trithio-α-L-arabinofuranoside (42) were isolated in 18% and 20% yield, respectively. The formation of these two derivatives is tentatively explained by involvement of a radical reaction mechanism. When O-(2,3-di-O-acetyl-4-azido-4-deoxy-5-thio-α-D-xylopyranosyl) trichloroacetimidate was used as donor and boron trifluoride ethyl etherate as promoter, 31 and 33 were formed in excellent yield (96%) in a 2:1 ratio. The glycosides, obtained on deacetylation of 33, 34, and 42 showed a significant antithrombotic activity on rats.