850883-53-3

Upstream product

• 97614-44-3 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide 
• 850883-58-8 bis(2-cyanoethyl)-2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl-1-phosphate 

Relevant academic research and scientific papers

Stereoselective synthesis of 2-deoxy-2-fluoroarabinofuranosyl-α-1- phosphate and its application to the synthesis of 2′-Deoxy-2′- fluoroarabinofuranosyl purine nucleosides by a chemo-enzymatic method

Stereoselective introduction of a phosphate moiety into 2-deoxy-2-fluoroarabinofuranose derivatives at the anomeric position was investigated by two methods. One involved a stereoselective hydrolysis of 1-bromo-derivative, and the consecutive phosphorylation of 2-deoxy-2-fluoro- α-D-arabinofuranose via a phosphoramidite derivative. The other method involved stereoselective α-phosphorylation of the 1-bromo-derivative at the 1-position. The resulting α-1-phosphate was utilized to prepare 2′-deoxy-2′-fluoroarabinofuranosyl purine nucleosides by an enzymatic glycosylation reaction. This chemo-enzymatic method will be applicable to the synthesis of some 2′F-araNs, and three important 2′F-araNs were actually obtained in 30-40% yields from 1,3,5-tri-O-benzoyl-2-deoxy-2- fluoro-α-D-arabinose with high purity.

ALPHA-1-PHOSPHORYLATED-2-DEOXY-2-FLUOROARABINOSIDE AND PROCESS FOR PRODUCING 2 -DEOXY-2 -FLUORO-BETA-D-ARABINONUCLEOSID E

A method for producing 2'-deoxy-2'-fluoro-β-D-arabinonucleoside represented by formula (II): (wherein B represents a base), in particular, 2'-deoxy-2'-fluoro-β-D-arabinopurinenucleoside, which method comprises causing a nucleoside phosphorylase to act on α-1-phosphorylated-2-deoxy-2-fluoroarabinoside represented by formula (I): or a mixture of α- and β-isomers of 1-phosphorylated-2-deoxy-2-fluoroarabinoside represented by formula (V'): and on a base. The compound can be produced at high yield and in a convenient and highly stereoselective manner.