219627-15-3

Basic information

• Product Name: Acetic acid (2R,3S,4S,5R)-4-acetoxy-5-acetoxymethyl-2-p-tolylsulfanyl-tetrahydro-furan-3-yl ester
• Synonyms: Acetic acid (2R,3S,4S,5R)-4-acetoxy-5-acetoxymethyl-2-p-tolylsulfanyl-tetrahydro-furan-3-yl ester
• CAS NO: 219627-15-3
• Molecular Weight: 382.434
• Mol File: 219627-15-3.mol

Chemical Properties

• CAS DataBase Reference: Acetic acid (2R,3S,4S,5R)-4-acetoxy-5-acetoxymethyl-2-p-tolylsulfanyl-tetrahydro-furan-3-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid (2R,3S,4S,5R)-4-acetoxy-5-acetoxymethyl-2-p-tolylsulfanyl-tetrahydro-furan-3-yl ester(219627-15-3)
• EPA Substance Registry System: Acetic acid (2R,3S,4S,5R)-4-acetoxy-5-acetoxymethyl-2-p-tolylsulfanyl-tetrahydro-furan-3-yl ester(219627-15-3)

Safety Data

• Hazardous Substances Data: 219627-15-3(Hazardous Substances Data)

Upstream product

• 39727-26-9 β-D-Ribofuranose-1,2,3,5-tetraacetate 
• 106-45-6 para-thiocresol 

Downstream Products

• 219627-25-5 octyl 5-O-(2,3,5-tri-O-acetyl-α-D-lyxofuranosyl)-2,3-di-O-benzyl-α-D-arabinofuranoside 
• 219627-26-6 Benzoic acid (2S,3S,4R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-((2R,3S,4S,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-2-methoxy-tetrahydro-furan-3-yl ester 
• 219627-24-4 methyl 5-O-(2,3,5-tri-O-acetyl-α-D-lyxofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside 
• 110415-60-6 methyl 2,3,5-tri-O-acetyl-α-D-lyxofuranoside 

Relevant articles and documents

Conversion of pyranose glycals to furanose derivatives: A new route to oligofuranosides

Acetylated pyranose glycals have been converted through a convenient three-step process into protected furanose reducing sugars. Ozonolysis of 2,3,5-tri-O-acetyl-glucal or 2,3,5-tri-O-acetylgalactal, followed by treatment with dimethyl sulfide and then hydrolysis gave respectively protected arabinofuranose (6) and lyxofuranose (7) derivatives. Conversion of these hemiacetals to oligosaccharides was explored using a number of methods. Activation of 6 or 7 in situ afforded glycosides in modest yield and stereoselectivity. Glycosylation of tetraacetates 16 and 18, obtained from 6 and 7, gave similar results. However, thioglycosides 17 and 19, also derived from 6 and 7, were found to be effective glycosyl donors, producing products in good to excellent yields and with high stereoselectivities. The method was also used to synthesize a disaccharide in which one residue contained uniform 13C enrichment.