204918-59-2Relevant articles and documents
Arabinofuranosyl oligosaccharides from mycobacteria: Synthesis and effect of glycosylation on ring conformation and hydroxymethyl group rotamer populations
D'Souza, Francis W.,Ayers, Joseph D.,McCarren, Patrick R.,Lowary, Todd L.
, p. 1251 - 1260 (2007/10/03)
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
D'Souza, Francis W.,Cheshev, Pavel E.,Ayers, Joseph D.,Lowary, Todd L.
, p. 9037 - 9044 (2007/10/03)
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.