288160-40-7

Upstream product

• 189949-27-7 (R)-3-hydroxy-4-(2-indolyl)butyronitrile 
• 252191-39-2 {(R)-4-[(2R,3S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-1,2-dihydro-3-oxa-4a-aza-4-phospha-fluoren-2-yl}-acetonitrile 
• 252191-34-7 (R)-1-tert-butyldimethylsilyloxy-3-(1-phenylsulfonylindol-2-yl)propan-2-ol 
• 189949-24-4 (R)-3-indol-2-yl-2-hydroxypropanyl p-toluenesulfonate 
• 189949-23-3 (R)-3-(indol-2-yl)propane-1,2-diol 
• 40733-28-6 5'-tert-butyldimethylsilyloxy-2'-deoxythymidine 

Relevant academic research and scientific papers

Indolyl-oxazaphosphorine Precursors for Stereoselective Synthesis of Phosphite Triesters and Dithymidinyl Phosphorothioates

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.