The stereospecific synthesis of P-chiral biophosphates and their analogues by the Stec reaction

摘要

This manuscript summarizes the results of studies on the application of the reaction of dialkyl (aryl) phosphor-amidate anions with carbonyl electrophiles for stereospecific synthesis of P-chiral biophosphates (Stec reaction). Following the results obtained with organic phosphor-amidates which delineated the scope of the reaction and its stereochemical course, the application of the title reaction is presented for the preparation of diastereomerically pure P-chiral cyclic nucleotide analogues (phosphorothioates, phos-phoroselenoates, phosphoroselenothioates, isotopomeric ~(18)O-phosphates), and P-chiral nucleoside monophosphate analogues, as well as dinucleoside phosphate analogues (phosphorothioates, methanephosphonates).