Synthesis of Enol Adenosine 5-Phosphate Derivatives by the Perkow Reaction of a Silylated Adenosine 5-Phosphonate Derivative with α-Halo Ketones

Title: Synthesis of Enol Adenosine 5-Phosphate Derivatives by the Perkow Reaction of a Silylated Adenosine 5-Phosphonate Derivative with α-Halo Ketones

Volume: 1 Issue: 3

Author(s): Tomohisa Moriguchi, Kazuhisa Okada, Kohji Seio and Mitsuo Sekine

Affiliation:

Keywords: enol phosphate, pyrophosphate, the perkow reaction, nucleotides

Abstract: This paper deals with the synthesis of α-substituted enol ester derivatives of adenosine 5- phosphate. These compounds were formed by the Perkow reaction of α-chloromethyl ketones with an in situgenerated adenosine-5-yl bis(trimethylsilyl) phosphite intermediate. Among these reactions, the use of α- chloro-2,4-difluoroacetophenone gave predominantly the enol phosphate derivative over the Arbuzov reaction product and the carbonyl adduct, which were formed as byproducts.

Cite this article as:

Moriguchi Tomohisa, Okada Kazuhisa, Seio Kohji and Sekine Mitsuo, Synthesis of Enol Adenosine 5-Phosphate Derivatives by the Perkow Reaction of a Silylated Adenosine 5-Phosphonate Derivative with α-Halo Ketones, Letters in Organic Chemistry 2004; 1 (3) . https://dx.doi.org/10.2174/1570178043401225