Improved Synthesis of 1,3-Propanediol Derivatives Having a Diethoxyphosphoryldifluoroethyl Functional Group at the 2-Position: Application to Chemoenzymatic Synthesis of Novel Acyclic Nucleotide Analogues of Adenosine Bisphosphates

Tetsuo Murano; Hirokuni Kobayakawa; Yoko Yuasa; Tsutomu Yokomatsu; Shiroshi Shibuya

doi:10.1055/s-2004-834941

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Improved Synthesis of 1,3-Propanediol Derivatives Having a Diethoxyphosphoryldifluoroethyl Functional Group at the 2-Position: Application to Chemoenzymatic Synthesis of Novel Acyclic Nucleotide Analogues of Adenosine Bisphosphates

Tetsuo Murano, Hirokuni Kobayakawa, Yoko Yuasa, Tsutomu Yokomatsu*, Shiroshi Shibuya
School of Pharmacy, Tokyo University of Pharmacy & Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Fax: +81(426)763239; e-Mail: yokomatu@ps.toyaku.ac.jp;

Abstract

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Abstract

An alternative synthesis of 1,3-propanediol 1 having a diethoxyphosphoryldifluoroethyl group was examined. The method readily provided a multi-gram quantity of 1. The propanediol 1 was chemo-enzymatically transformed to acyclic nucleotide analogues for adenosine bisphosphates.

Key words

1,3-propanediols - fluorine - transesterifications - chiral pool - nucleotide analogues

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