Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, K.U. Leuven, Leuven B-3000, Belgium.
J Org Chem. 2011 May 20;76(10):3742-53. doi: 10.1021/jo200033p. Epub 2011 Apr 18.
The synthesis of (E)-3'-phosphonoalkenyl and 3'-phosphonoalkyl modified nucleoside analogues with a β-D-erythrofuranose moiety is reported. The highly stereoselective olefin cross-metathesis reaction was applied to introduce the phosphonoalkenyl group at the 3'-position of the sugar moiety with absolute (E)-selectivity. The 3',6'-cyclomonophosphonic acids of 3'-phosphonoethyl-β-D-erythrofuranosyl nucleosides were synthesized via a dehydrative intramolecular cyclization reaction. None of the synthesized compounds shows significant in vitro activity against HIV, HCV, and RSV.
报道了具有β-D-赤式呋喃糖部分的（E）-3'-膦烯基和 3'-膦烷基修饰核苷类似物的合成。高度立体选择性的烯烃交叉复分解反应被应用于在糖部分的 3'-位引入磷烯基，具有绝对的（E）选择性。通过脱水分子内环化反应合成了 3'-膦乙基-β-D-赤式呋喃核苷的 3'，6'-环单磷酸。所合成的化合物对 HIV、HCV 和 RSV 均没有显著的体外活性。
