402759-14-2

Downstream Products

• 1448225-81-7 methyl 5-O-{3,5-di-O-(2-O-[2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl]-3,5-di-O-benzyl-α-D-arabinofuransoyl)-2-O-benzyl-α-D-arabinofuranosyl}-2,3-di-O-benzyl-α-D-arabinofuranoside 
• 527682-43-5 methyl 5-O-{3,5-di-O-(2-O-[2,3-anhydro-5-O-benzoyl-β-D-arabinofuranosyl]-3,5-di-O-benzyl-α-D-arabinofuranosyl)-2-O-benzyl-α-D-arabinofuranosyl}-2,3-di-O-benzyl-α-D-arabinofuranoside 

Relevant academic research and scientific papers

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-

Influence of Steric Crowding on Diastereoselective Arabinofuranosylations

The occurrence of arabinofuranosides on the cell surface of Mycobacterium tuberculosis (Mtb) and their significance in controlling disease spurred interest in developing strategies for their diastereoselective synthesis. Mtb uses enzymes to achieve diastereoselectivity through noncovalent interactions. Of the two possible glycosidic linkages, chemically, 1,2-trans linkage is relatively easy to synthesize by taking advantage of neighboring group participation, whereas synthesis of the 1,2-cis linkage is notoriously difficult. In this article, stereochemical effects on the diastereoselectivity of arabinofuranosidation are investigated with thiopyridyl, imidate, and thiotolyl donors as well as differently crowded glycosyl acceptors; subtle differences in the stereochemical environment of the acceptors were observed to alter the diastereoselectivity of the furanoside formation. Results from this endeavor suggest that 1,2-cis arabinofuranosides can be synthesized conveniently by conducting the reaction at lower temperature on sterically demanding and less reactive substrates.

β-arabinofuranosylation using 5- O -(2-quinolinecarbonyl) substituted ethyl thioglycoside donors

A new β-stereoselective d- and l-arabinofuranosylation method has been developed employing 5-O-(2-quinolinecarbonyl) substituted arabinosyl ethyl thioglycosides as glycosyl donors. The approach allows a wide range of acceptor substrates to be used; the β-selectivity is good-to-excellent. Stereoselective synthesis of a mannose-capped octasaccharide portion from a mycobacterial cell wall polysaccharide was then carried out to demonstrate the utility of this methodology.

Arabinofuranosides from mycobacteria: Synthesis of a highly branched hexasaccharide and related fragments containing β-arabinofuranosyl residues

The synthesis of 11 oligosaccharides (4-14) containing β-arabinofuranosyl residues is reported. The glycans are all fragments of two polysaccharides, arabinogalactan and lipoarabinomannan, which are found in the cell wall complex of mycobacteria. In the preparation of the targets, the key step was a low-]temperature glycosylation reaction that installed the β-arabinofuranosyl residues with good to excellent stereocontrol.