189949-21-1Relevant articles and documents
Indolyl-oxazaphosphorine Precursors for Stereoselective Synthesis of Phosphite Triesters and Dithymidinyl Phosphorothioates
Wang, Jian-Chao,Just, George
, p. 8090 - 8097 (1999)
Several novel chiral indolyl-oxazaphosphorines 7 were synthesized, and their potential as precursors to chiral phosphorothioates was evaluated. Reaction of 7 with a thymidine derivative gave phosphite triester 8 with a large degree of stereoselectivity. Sulfurization with Beaucage's reagent provided phosphorothioate triesters 9. The chiral auxiliary 9b containing a cyano group could be easily removed with aqueous ammonia to form dithymidinyl phosphorothioate in more than 97% diastereomeric excess. The chiral indolyl-oxazaphosphorines 7 are a new class of precursors for stereoselective synthesis of phosphorothioates.