Department of Bioorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90-363 Łódź, Poland.
Chirality. 2011 Mar;23(3):237-44. doi: 10.1002/chir.20905. Epub 2010 Oct 6.
A method for stereocontrolled chemical synthesis of P-substituted nucleoside 5'-O-phosphorothioates has been elaborated. Selected 3'-O-acylated deoxyribonucleoside- and 2',3'-O,O-diacylated ribonucleoside-5'-O-(2-thio-4,4-pentamethylene-1,3,2-oxathiaphospholane)s were chromatographically separated into P-diastereomers. Their reaction with anions of phosphorus-containing acids was highly stereoselective (≥90%) and furnished corresponding P-chiral α-thiodiphosphates and their phosphonate analogs with satisfactory yield.
已经详细阐述了一种对映选择性控制的 P-取代核苷 5'-O-膦酸硫酯的化学合成方法。选择的 3'-O-酰化脱氧核苷和 2',3'-O,O-二酰化核糖核苷-5'-O-(2-硫代-4,4-戊亚甲基-1,3,2-氧杂硫杂环戊烷)通过色谱分离成 P-非对映异构体。它们与含磷酸的阴离子的反应具有高度的对映选择性（≥90%），并以令人满意的收率得到相应的 P-手性α-硫代二磷酸酯及其膦酸酯类似物。
