329360-17-0

Basic information

• Product Name: p-tolyl 2,3-anhydro-5-O-benzoyl-1-thio-α-D-lyxofuranoside
• Synonyms: p-tolyl 2,3-anhydro-5-O-benzoyl-1-thio-α-D-lyxofuranoside
• CAS NO: 329360-17-0
• Molecular Weight: 342.416
• Mol File: 329360-17-0.mol

Chemical Properties

• CAS DataBase Reference: p-tolyl 2,3-anhydro-5-O-benzoyl-1-thio-α-D-lyxofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: p-tolyl 2,3-anhydro-5-O-benzoyl-1-thio-α-D-lyxofuranoside(329360-17-0)
• EPA Substance Registry System: p-tolyl 2,3-anhydro-5-O-benzoyl-1-thio-α-D-lyxofuranoside(329360-17-0)

Safety Data

• Hazardous Substances Data: 329360-17-0(Hazardous Substances Data)

Upstream product

• 65-85-0 benzoic acid 
• 204918-49-0 p-methylphenyl 1-thio-α-D-arabinofuranoside 

Downstream Products

• 329360-25-0 n-octyl 2,3-anhydro-5-O-benzoyl-β-D-lyxofuranoside 
• 352438-16-5 p-tolyl 2,3-anhydro-1-thio-α-D-lyxofuranoside 
• 527681-58-9 methyl 6-O-(2,3-anhydro-5-O-benzoyl-β-D-lyxofuranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 329360-36-3 methyl 5-O-[5-O-(2,3-anhydro-5-O-benzoyl-β-D-lyxofuranosyl)-2,3-anhydro-α-D-lyxofuranosyl]-2,3-anhydro-α-D-lyxofuranoside 
• 1185748-17-7 3-(5-O-benzoyl-2-deoxy-2-(p-thiotolyl)-β-D-xylofuranosyl)-1-propene 
• 1185748-16-6 5-O-benzoyl-2-deoxy-2-(p-thiotolyl)-β-D-xylofuranosyl azide 
• 1185748-20-2 2-(3,5-O-isopropylidene-2-deoxy-2-(p-thiocresyl)-β-D-xylofuranosyl)acetophenone 
• 1185748-21-3 2-(3,5-O-isopropylidene-2-deoxy-2-(p-thiocresyl)-β-D-xylofuranosyl)-1-(R/S)-phenyl ethanol 
• 1185748-19-9 1-(3,5-O-isopropylidene-2-deoxy-2-(p-thiocresyl)-α-D-xylofuranosyl)-3-propene 
• 1185748-18-8 2-(5-O-benzoyl-2-deoxy-2-(p-thiotolyl)-β-D-xylofuranosyl)acetophenone 

Relevant articles and documents

2,3-Anhydro sugars in glycoside bond synthesis. Highly stereoselective syntheses of oligosaccharides containing α- and β-arabinofuranosyl linkages

The ever-increasing discovery of biologically important events mediated by carbohydrates has generated great interest in the synthesis of oligosaccharides and the development of new methods for glycosidic bond formation. In this paper, we report that 2,3-

Sensitivity of 1JC1-H1 magnitudes to anomeric stereochemistry in 2,3-anhydro-O-furanosides

The magnitude of the one-bond coupling constant between C1 and H1 in 2,3-anhydro-O-furanosides has been shown to be sensitive to the stereochemistry at the anomeric center. A panel of 24 compounds was studied and in cases where the anomeric hydrogen is trans to the epoxide moiety, 1JC1-H1 = 163 - 168 Hz; and when this hydrogen is cis to the oxirane ring, 1JC1-H1 = 171 - 174 Hz. In contrast, for 2,3-anyhdro-S-glycosides, the size of the 1JC1-H1 is not sensitive to C1 stereochemistry. Computational studies on all four methyl 2,3-anhydro-O-furanosides (5-8) demonstrated that 1JC1-H1 was inversely proportional to the length of the C1-H1 bond. A previously reported equation, which relates C1-H1 bond distance and atomic charges to 1JC1-H1 magnitudes, could be used to accurately predict the J values in the α-lyxo (5) and β-ribo (8) isomers. In contrast, with the β-lyxo (6) and α-ribo isomers (7), this equation underestimated the size of these coupling constants by 10-20 Hz.

Stereocontrolled synthesis of 2,3-anhydro-β-D-lyxofuranosyl glycosides

(Matrix presented) The stereocontrolled synthesis of 2,3-anhydro-β-D-lyxofuranosyl glycosides from thioglycoside 2 and glycosyl sulfoxide 3 is reported.