A new facile, rapid, stereo- and regio-selective one-pot synthesis of nucleoside-2’,3’-O,O-phosphorothioate and selenoate analogs has been developed. The method is based on the DBU-assisted ring-opening of new reagents, 2-cyanoethoxy-thio and seleno–dithiaphospholane by uridine, producing Sp-uridine 2’,3’-O,O-phosphorothioate or selenoate in good yields. This method avoids the need for protection strategies and chiral reagents, chiral metal catalysts, or chiral separations. The kinetic product was the Sp epimer, while at elevated temperatures both Sp and Rp epimers were obtained. This synthetic method has been applied to all natural nucleosides (U/A/G/C/T). Furthermore, we have deciphered the origin of the stereo- and regio-selectivity of the reaction

DBU-assisted nucleophilic ring-opening dithia-/oxathia-phospholane (addressing regio- and stereo-specificity challenges in the synthesis of nucleoside 2′,3′-cyclic monophosphate)

ACS Spring Meeting 2021

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