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Ex-Chiral-Pool Synthesis of β-Hydroxyphosphonate Nucleoside Analogues

✍ Scribed by Franck Gallier; Suzanne Peyrottes; Christian Périgaud

Publisher: John Wiley and Sons
Year: 2007
Tongue: English
Weight: 183 KB
Volume: 2007
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200600562

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✦ Synopsis

Abstract

A new series of mononucleotide analogues bearing a nonhydrolysable P–C bond instead of the P–O phosphate linkage is presented. We intend to set up an approach that allows the synthesis of β‐hydroxyphosphonate nucleoside analogues as a single diastereoisomer. In this respect, the key “sugar‐phosphonate” intermediate was obtained through an Arbusov reaction from an iodosugar derivative in which the stereochemistry of the β‐hydroxy group is determined by the choice of the starting material and remains in the resulting nucleotide analogues. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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