310880-56-9

Upstream product

• 645-96-5 Benzeneselenol 
• 282107-50-0 3-O-benzyl-β-D-arabinofuranose 1,2,5-orthobenzoate 
• 100-39-0 benzyl bromide 
• 7473-42-9 methyl tri-O-benzoyl-α-D-arabinofuranoside 
• 282107-49-7 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 
• 502761-66-2 C₁₃H₁₆O₆C₁₄H₈O₂ 

Downstream Products

• 502761-84-4 phenyl 2-O-benzoyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-1-seleno-α-D-arabinofuranoside 
• 502761-85-5 phenyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-1-seleno-α-D-arabinofuranoside 

Relevant academic research and scientific papers

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.

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.