204918-59-2

Upstream product

• 61826-42-4 tetra-O-acetyl-D-arabinofuranose 
• 90244-44-3 methyl 2,3,5-tri-O-acetyl-α,β-D-arabinofuranoside 
• 79083-42-4 methyl D-arabinofuranoside 
• 98-88-4 benzoyl chloride 
• 28697-53-2 D-arabinopyranose 
• 64609-15-0 2,3,5-tri-O-acetyl-D-arabinofuranose 
• 56607-40-0 methyl D-arabinofuranoside 
• 204918-51-4 methyl 2,3-di-O-benzoyl-α-D-arabinofuranoside 
• 204918-48-9 1-(p-thiocresyl)-2,3,5-tri-O-acetyl-α-D-arabinofuranoside 
• 204918-50-3 methyl 2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranoside 

Relevant academic research and scientific papers

Arabinofuranosyl oligosaccharides from mycobacteria: Synthesis and effect of glycosylation on ring conformation and hydroxymethyl group rotamer populations

A series of αD-arabinofuranosyl oligosaccharides (2-8) that are fragments of the arabinan portions of two polysaccharides present in the cell wall of Mycobacterium tuberculosis have been synthesized. Preparation of the oligosaccharides involved the sequen

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.

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.