Ex-chiral-pool synthesis of beta-hydroxyphosphonate nucleoside analogues

1434 193x EnglishInternational audienceA 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 beta-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 beta-hydroxy group is determined by the choice of the starting material and remains in the resulting nucleotide analogues. ((C) Wiley-VCH Verlag GmbH and Co. KGaA, 69451 Weinheim, Germany, 2007)