282107-63-5

Upstream product

• 7473-42-9 methyl tri-O-benzoyl-α-D-arabinofuranoside 
• 100-39-0 benzyl bromide 
• 502761-66-2 C₁₃H₁₆O₆C₁₄H₈O₂ 
• 34957-73-8 methyl 9-hydroxynonanoate 
• 282107-50-0 3-O-benzyl-β-D-arabinofuranose 1,2,5-orthobenzoate 
• 502761-67-3 (3aS,5R,6R,6aS)-5-Hydroxymethyl-2-methoxy-2-phenyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 
• 282107-49-7 β-D-arabinofuranose 1,2,5-orthobenzoate 

Downstream Products

• 628686-38-4 8-(methoxycarbonyl)octyl 2-O-benzoyl-5-O-(2-O-benzoyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranosyl)-3-O-benzyl-α-D-arabinofuranoside 
• 628686-54-4 8-(methoxycarbonyl)octyl 2-O-benzoyl-5-O-[2-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-α-D-arabinofuranosyl]-3-O-benzyl-α-D-arabinofuranoside 
• 628686-45-3 8-(methoxycarbonyl)octyl 2-O-benzoyl-5-O-{2-O-benzoyl-5-O-[2-O-benzoyl-3,5-di-O-(1,1,3,3-tetra-isopropyldisiloxan-1,3-diyl)-α-D-arabinofuranosyl]-3-O-benzyl-α-D-arabinofuranosyl}-3-O-benzyl-α-D-arabinofuranoside 
• 628686-46-4 8-(methoxycarbonyl)octyl 2-O-benzoyl-5-O-[2-O-benzoyl-5-O-(2-O-benzoyl-α-D-arabinofuranosyl)-3-O-benzyl-α-D-arabinofuranosyl]-3-O-benzyl-α-D-arabinofuranoside 
• 628686-39-5 8-(methoxycarbonyl)octyl 2-O-benzoyl-5-O-(2-O-benzoyl-3-O-benzyl-α-D-arabinofuranosyl)-3-O-benzyl-α-D-arabinofuranoside 

Relevant academic research and scientific papers

Elaboration of monoarabinofuranosidic building blocks

Nucleophilic opening of 1,2,5-orthoesters 1, 2 and 6 of D-arabinose with alcohols, ethanethiol and selenophenol was carried out under very mild conditions with Lewis acid catalysis. The reaction is stereoselective and gave α-D-arabinofuranosides in high yields. Various monoarabinofuranosides, thio-and selenoglycoside donors as well as acceptors were obtained in few steps from the opening products. These building blocks define a comprehensive system of glycosylation for the synthesis of any glycosidic linkage between arabino-furanosides. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

1,2,5-Ortho esters of D-arabinose as versatile arabinofuranosidic building blocks. Concise synthesis of the tetrasaccharidic cap of the lipoarabinomannan of Mycobacterium tuberculosis

1,2,5-ortho esters of D-arabinose were found to be ideally suited building blocks for the stereoselective formation of and β arabinofuranosidic linkages after nucleophilic opening of the orthoester with oxygen and sulfur nucleophiles; the tetrasaccharidic cap of the lipoarabinomannan of Mycobacterium tuberculosis was then synthesized in a highly convergent manner.

A comprehensive glycosylation system for the elaboration of oligoarabinofuranosides

1,2,5-Orthoesters of D-arabinose are key compounds for the construction of a glycosylation system that allows the stereoselective synthesis of any interglycosidic linkage between arabinofuranosidic units. Application to the synthesis of a pentaarabinofuranoside of the mycobacterial cell wall is also described. (C) 2000 Elsevier Science Ltd.