402758-89-8

Upstream product

• 329360-22-7 1-O-methyl-3,5-di-O-benzyl-α-D-arabinofuranose 
• 160549-10-0 2,3,5-tri-O-benzyl-D-arabinofuranose 
• 278796-50-2 p-cresyl 2,3,5-tri-O-benzyl-1-thio-D-arabinofuranoside 
• 205485-61-6 2-((3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylsulfanyl)-pyridine 
• 60933-68-8 3,4,6-tri-O-benzyl-β-D-arabinofuranoside 
• 62255-44-1 1-O-acetyl-2,3,5-tris-O-(benzyl)-α, β-D-arabinofuranose 

Relevant academic research and scientific papers

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.

Stereospecific Furanosylations Catalyzed by Bis-thiourea Hydrogen-Bond Donors

We report a new method for stereoselective O-furanosylation reactions promoted by a precisely tailored bis-thiourea hydrogen-bond-donor catalyst. Furanosyl donors outfitted with an anomeric dialkylphosphate leaving group undergo substitution with high anomeric selectivity, providing access to the challenging 1,2-cis substitution pattern with a range of alcohol acceptors. A variety of stereochemically distinct, benzyl-protected glycosyl donors were engaged successfully as substrates. Mechanistic studies support a stereospecific mechanism in which rate-determining substitution occurs from a catalyst-donor resting-state complex.

Acceptor-dependent stereoselective glycosylation: 2′-CB glycoside-mediated direct β-D-arabinofuranosylation and efficient synthesis of the octaarabinofuranoside in mycobacterial cell wall

(Chemical Equation Presented) A reliable and generally applicable direct method for the stereoselective β-arabinofuranosylation employing a 2′-carboxybenzyl arabinofuranoside as the glycosyl donor has been established. The acyl-protective group on glycosy

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.