204918-49-0

Upstream product

• 352438-38-1 p-tolyl 2,3,5-tri-O-benzoyl-1-thio-α-D-arabinofuranoside 
• 61826-42-4 tetra-O-acetyl-D-arabinofuranose 
• 90244-44-3 methyl 2,3,5-tri-O-acetyl-α,β-D-arabinofuranoside 
• 106-45-6 para-thiocresol 
• 79083-42-4 methyl D-arabinofuranoside 
• 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 
• 13035-61-5 1,2,3,5-tetra-O-acetyl-α-D-arabinofuranose 

Downstream Products

• 685111-66-4 p-toluyl 5-O-triphenylmethyl-1-thio-α-D-arabinofuranoside 
• 651706-56-8 p-toluyl 5-O-p-toluenesulfonyl-1-thio-α-D-arabinofuranoside 
• 917590-98-8 p-tolyl 3,5-O-(di-tert-butylsilanediyl)-1-thio-α-D-arabinofuranoside 
• 932719-57-8 methyl 2-O-benzyl-3,5-O-(di-tert-butylsilylene)-α-D-arabinofuranoside 

Relevant academic research and scientific papers

β-Selective xylulofuranosylation: Via a conformationally-restricted glycosyl donor

Reported is the first stereoselective method for β-xylulofuranosylation, which employs 3,4-O-xylylene-protected thioglycoside donors. For most acceptors, the best results were observed with a donor (8) that possesses both the xylylene group and a benzoate ester at O-1. To demonstrate its utility, the methodology was applied to the first synthesis of the pentasaccharide repeating unit from the lipopolysaccharide O-Antigen of Yersinia enterocolitica serovars O:5/O:5,27, a structure containing two β-xylulofuranose residues.

Efficient one-pot syntheses of α-d-arabinofuranosyl tri- and tetrasaccharides present in cell wall polysaccharide of Mycobacterium tuberculosis

Two α-d-arabinofuranosyl oligosaccharides (2 and 3) found as constituent parts of the polysaccharide portion from the cell wall of Mycobacterium tuberculosis have been efficiently synthesized via a one-pot glycosylation procedure in which a key step is th

β-selective arabinofuranosylation using a 2,3-o-xylylene-protected donor

Reported is a novel stereoselective β-arabinofuranosylation that makes use of a conformationally restricted 2,3-O-xylylene-protected arabinofuranosyl donor. Optimization of the reaction conditions showed that factors including the structure of the accepto

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.

Stereoselective synthesis of a fragment of mycobacterial arabinan

Strategies for the stereoselective synthesis of mycobacterial arabinan were explored. Arabinofuranosyl donors with various protective groups were screened in terms of suitability for β-(1,2-cis)-selective glycosylation. The protective group was found to affect the stereoselectivity of arabinofuranosylation. β-Selectivity was drastically enhanced by using donors protected with 3,5-TIDPS, possibly due to conformational constraints on the furanose ring. Synthesis of heptaarabinofuranoside was then performed to demonstrate the practicality of this methodology.

Synthetic arabinofuranosyl oligosaccharides as mycobacterial arabinosyltransferase substrates

A series of arabinofuranosyl oligosaccharides found as constituent parts of the polysaccharide portion of the cell wall of Mycobacterium tuberculosis have been chemically synthesized. Screening of these oligosaccharidss as substrates for arabinosyltransferases present in mycobacterial membrane preparations suggests that modified oligosaccharide analogs as small as disaccharides may be inhibitors of glycan biosynthesis. Such inhibitors would be of potential utility as lead compounds in the identification of new drugs for the treatment of mycobacterial infections.