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Nucleic Acids Symposium Series 2004 48(1):45-46; doi:10.1093/nass/48.1.45
© 2004 by Oxford University Press
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Practical synthesis of 2'-deoxy-2'-fluoroarabinofuranosyl purine nucleosides by chemo-emzymatic method

Kohei Yamada, Noritake Matsumoto and Hiroyuki Hayakawa

Biochemicals Division, Yamasa Corporation, 10-1 Araoichio 2-Chome, Choshi, Chiba 288-0056, Japan

Stereoselective introduction of a phosphate group into 2-fluorinated sugar (4) at the 1-position was developed by us for the first time. The resulting {alpha}-1-phosphate (1) was utilized to prepare 2'-deoxy-2'-fluoroarabino-furanosyl purine nucleosides (2), which were the key starting materials for the preparation of the 2'F-ANA-antisense molecule, by enzymatic glycosidation reaction. Next, we tried to apply this method as a practical synthesis of 2'F-araNs. Subsequently, we found an effect of additives on the direct phosphorylation of 1-bromide (4) with orthophosphoric acid. Tetra-n-butylammonium iodide was the most effective for achieving high {alpha}-selectivity among these additives. This reaction will be applicable for large-scale synthesis, and some 2'F-araNs were actually obtained in 30–40% yields from 1-O-benzoate (3). Thus, we proved the potency of the chemo-enzymatic synthesis of 2'F-ANs (2) by the use of {alpha}-1-phosphate (1).


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