181256-75-7

Upstream product

• 762-04-9 phosphonic acid diethyl ester 
• 117136-39-7 1-[(2R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-oxo-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 76-83-5 trityl chloride 

Downstream Products

• 181256-77-9 [(1R,2R,4R,5S)-2-(4-Hydroxy-2-oxo-2H-pyrimidin-1-yl)-4-trityloxymethyl-3,6-dioxa-bicyclo[3.1.0]hex-1-yl]-phosphonic acid diethyl ester 
• 181256-76-8 [(2R,3R,4R,5R)-3,4-Dihydroxy-2-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-5-trityloxymethyl-tetrahydro-furan-3-yl]-phosphonic acid diethyl ester 

Relevant academic research and scientific papers

Synthesis of nucleoside epoxyphosphonates

Reaction of two regioisomeric uridine derivatives, 1-[3-(diethoxyphosphinyl)-5-O-trityl-β-D-xylofuranosyl]uracil (4) and 1-[2-(diethoxyphosphinyl)-5-O-trityl-β-D-arabinofuranosyl]uracil (13), with triflyl chloride and 4-pyrrolidinopyridine (4-PDP) results in formation of the corresponding nucleoside epoxyphosphonates. This transformation is immediately useful for confirming the trans relationship of the 2'- and 3'-hydroxyl groups in the geminal hydroxyphosphonates 3 and 12, and provides access to two new families of nucleoside derivatives that may be of interest for their synthetic utility and biological properties.