56271-35-3

Upstream product

• 7473-42-9 methyl tri-O-benzoyl-α-D-arabinofuranoside 
• 79083-42-4 methyl D-arabinofuranoside 
• 1431370-38-5 (pent-4-enyl) 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside 
• 1824-96-0 Methyl α-lyxofuranoside 
• 98-88-4 benzoyl chloride 
• 532-20-7 D-arabinofuranose 

Downstream Products

• 81336-88-1 C₃₁H₃₄O₈Si 
• 38642-50-1 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl cyanide 
• 83416-39-1 1-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2-nitroimidazole 
• 83416-41-5 1-(2,3,5-tri-O-benzoyl-β-D-arabinofuranosyl)-2-nitroimidazole 
• 115957-00-1 4,6-dimethylthio-1-α-(2,3,5-tri-O-benzoyl-D-arabinofuranosyl)pyrazolo<3,4-d>pyrimidine 
• 115956-99-5 4,6-dimethylthio-1-β-(2,3,5-tri-O-benzoyl-D-arabinofuranosyl)pyrazolo<3,4-d>pyrimidine 
• 84588-48-7 2-(1-isopropylidene)azino-3-(2',3',5'-tri-o-benzoyl-α-D-arabinofuranosyl)-5-methoxycarbonylmethylenethiazolidine-4-one 
• 204716-47-2 C₂₆H₂₂O₈ 
• 765274-01-9 3,5-di-O-benzoyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate) 
• 1431370-38-5 (pent-4-enyl) 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside 
• 103702-71-2 benzyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside 
• 1431370-40-9 benzyl N-(benzyloxycarbonyl)-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-L-serinate 
• 1431370-42-1 methyl 2,3,6-tri-O-benzyl-4-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-glucopyranoside 
• 1431370-43-2 pent-4-enyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-mannopyranoside 

Relevant academic research and scientific papers

Gold(III)-catalyzed glycosidations for 1,2- trans and 1,2- cis furanosides

Stereoselective synthesis of furanosides is still a daunting task, unlike the pyranosides, for which several methods exist. Herein, a unified stereoselective strategy for the synthesis of 1,2-trans and 1,2-cis furanosides is revealed for seven out of eight possible isomers of pentoses. The identified protocol gives access to diastereoselective synthesis of α- and β-araf, ribf, lyxf, and α-xylf furanosides. 1,2-trans glycosides were synthesized by the use of propargyl 1,2-orthoesters under gold-catalyzed glycosidation conditions, and subsequently, they are converted into 1,2-cis glycosides through oxidation-reduction as the key functional group transformation. All the reactions are found to be fully diastereoselective, mild, and high yielding.

Efficient synthesis of oligosaccharyl 1,2-O-orthoesters from n-pentenyl glycosides and application to the pentaarabinofuranoside of the mycobacterial cell surface

Complex oligosaccharide syntheses employ the use of more than one glycosyl donor and hence, methods for the interconversion of glycosyl donors are highly valuable for the overall synthesis plan. Herein, n-pentenyl glycosides are efficiently converted to g

Facile synthesis of β- And α-arabinofuranosides and application to cell wall motifs of M. tuberculosis

Propargyl 1,2-orthoesters of arabinose are exploited for the synthesis of 1,2-trans furanosides; easily accessible 1,2-trans ribofuranosides are converted to challenging 1,2-cis-arabinofuranosides by oxidoreduction. Utility of these protocols was demonstrated by the successful synthesis of major structural motifs present in the cell surface of Mycobacterium tuberculosis. Key furanosylations were carried out under gold-catalyzed glycosidation conditions.

Ready preparation of furanosyl n-pentenyl orthoesters from corresponding methyl furanosides

The 3,5-di-O-benzoyl n-pentenyl orthoesters of the four pentofuranoses have been prepared. The first key intermediate in each case is the methyl pentofuranoside(s), and a user-friendly procedure for the preparation of each, based on the Callam-Lowary precedent, is described, whereby formation of the crucial α/β anomeric mixture is optimized. The mixture is used directly to prepare the corresponding perbenzoylated pentofuranosyl bromide(s) and then the title compounds.

Synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan

Mycolyl-arabinogalactan (mAG) complex is a major component of the cell wall of Mycobacterium tuberculosis, the causative agent of tuberculosis disease. Due to the essentiality of the cell wall for mycobacterium viability, knowledge of the biosynthesis of

Synthesis of 4-deoxy-4-thioarabinofuranosyl disaccharides, analogs of Mycobacterial arabinogalactan

The first chemical synthesis of disaccharides, octyl 5-O-(4-deoxy-4-thio- α-D-arabinofuranosyl)-α-D-arabinofuranoside 1 and octyl 5-O-(4-deoxy-4-thio-β-D-arabinofuranosyl)-α-D-arabinofuranoside 2 incorporating 4-deoxy-4-thioarabinose is described. Designed to mimic components of mycobacterial arabinogalactan, a major and essential constituent of the cell wall of tuberculosis and related bacteria, the compounds may disrupt cell wall biogenesis. A variety of coupling methods have been investigated before finding satisfactory techniques useful for thiofuranoses. Reductive deprotection of the sulfur-containing species is problematic, though lithium naphthalenide has proved to be an effective technique.

An improved synthesis of α-AZA, α-AZP and α-AZG, the precursors to clinical markers of tissue hypoxia

α-[123I]-IAZA and α-[123I]-IAZP are experimental diagnostic radiopharmaceuticals which have been used clinically to diagnose hypoxia in a number of pathologies, including cancer, peripheral vascular disease, rheumatoid arthritis and brain trauma. These nitroimidazole nucleosides are synthesized from the non-iodinated nucleosides AZA, AZP and AZG, respectively. Earlier methods report low chemical yields for the synthesis of these precursors. The modified procedures now reported provide nearly quantitative yields of these compounds, thereby substantially reducing the cost and effort of synthesis.