917590-98-8

Basic information

• Product Name: p-tolyl 3,5-O-(di-tert-butylsilanediyl)-1-thio-α-D-arabinofuranoside
• Synonyms: p-tolyl 3,5-O-(di-tert-butylsilanediyl)-1-thio-α-D-arabinofuranoside
• CAS NO: 917590-98-8
• Molecular Weight: 396.623
• Mol File: 917590-98-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: p-tolyl 3,5-O-(di-tert-butylsilanediyl)-1-thio-α-D-arabinofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: p-tolyl 3,5-O-(di-tert-butylsilanediyl)-1-thio-α-D-arabinofuranoside(917590-98-8)
• EPA Substance Registry System: p-tolyl 3,5-O-(di-tert-butylsilanediyl)-1-thio-α-D-arabinofuranoside(917590-98-8)

Safety Data

• Hazardous Substances Data: 917590-98-8(Hazardous Substances Data)

Upstream product

• 917590-92-2 p-tolyl 5-O-t-butyldiphenylsilyl-2,3-di-O-acetyl-1-thio-α-D-arabinofuranoside 
• 845868-93-1 1,2,3-tri-O-acetyl-5-O-t-butyldiphenylsilyl-D-arabinofuranose 
• 204918-48-9 1-(p-thiocresyl)-2,3,5-tri-O-acetyl-α-D-arabinofuranoside 
• 106-45-6 para-thiocresol 
• 13035-61-5 1,2,3,5-tetra-O-acetyl-α-D-arabinofuranose 
• 85272-31-7 di-tert-butylsilyl bis(trifluoromethanesulfonate) 
• 204918-49-0 p-methylphenyl 1-thio-α-D-arabinofuranoside 
• 18395-90-9 Di-tert-butyldichlorosilane 

Downstream Products

• 1207338-46-2 C₂₇H₃₆O₅SSi 
• 402758-82-1 methyl 2-O-benzyl-α-D-arabinofuranoside 
• 932719-69-2 methyl 2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-α-D-arabinofuranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 932719-57-8 methyl 2-O-benzyl-3,5-O-(di-tert-butylsilylene)-α-D-arabinofuranoside 
• 932719-13-6 p-tolyl 2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-1-thio-α-D-arabinofuranoside 
• 917590-99-9 p-tolyl 3,5-O-(di-tert-butylsilylene)-1-thio-2-O-triisopropylsilyl-α-D-arabinofuranoside 

Relevant articles and documents

Ligand specificity of CS-35, a monoclonal antibody that recognizes mycobacterial lipoarabinomannan: A model system for oligofuranoside-protein recognition

The CS-35 antibody is widely used in the characterization of glycans containing D-arabinofuranose residues, in particular polysaccharides present in the mycobacterial cell wall. A detailed understanding of the combining site of this antibody and the measu

On the use of 3,5-O-benzylidene and 3,5-O-(Di-tert-butylsilylene)-2-O- benzylarabinothiofuranosides and their sulfoxides as glycosyl donors for the synthesis of β-arabinofuranosides: Importance of the activation method

A 2-O-benzyl-3,5-O-benzylidene-α-D-thioarabinofuranoside was obtained by reaction of the corresponding diol with α,α-dibromotoluene under basic conditions. On activation with 1-benzenesulfinyl piperidine, or diphenyl sulfoxide, and trifluoromethanesulfonic anhydride in dichloromethane at -55 °C, reaction with glycosyl acceptors affords anomeric mixtures with little or no selectivity. The analogous 2-O-benzyl-3,5-O-(di-tert-butylsilylene)- α-D-thioarabinofuranoside also showed no significant selectivity under the 1-benzenesulfinyl piperidine or diphenyl sulfoxide conditions. With N-iodosuccinimide and silver trifluoromethanesulfonate the silylene acetal showed moderate to high β-selectivity, independent of the configuration of the starting thioglycoside. High β-selectivity was also obtained with a 2-O-benzyl-3,5-O-(di-tert-butylsilylene)-α-arabinofuranosyl sulfoxide donor on activation with trifluoromethanesulfonic anhydride. The high β-selectivities obtained by the N-iodosuccinimide/silver trifluoromethanesulfonate and sulfoxide methods are consistent with a common intermediate, most likely to be the oxacarbenium ion. The poor selectivity observed on activation of the thioglycosides with the 1-benzenesulfinyl piperidine, or diphenyl sulfoxide, and trifluoromethanesulfonic anhydride methods appears to be the result of the formation of a complex mixture of glycosyl donors, as determined by low-temperature NMR work.