181047-30-3

Upstream product

• 1666-13-3 diphenyl diselenide 
• 7354-93-0 2',3'-O-isopropylidene-5'-O-tosyluridine 
• 181047-06-3 1-((3aR,4R,6S,6aS)-2,2-Dimethyl-6-phenylselanylmethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Uridine 5'-monoselenoacetals as substrates for diastereoselective homolytic C-C bond formation

Uridine 5'-monoselenoacetals prepared by the seleno-Pummere reaction of 5'-deoxy-5'-phenylselenouridines were used as substrates for radical-mediated reactions with allyltributyltin. The reaction of the 2',3'-O-isopropylidene derivative gave cyclized products, 5-allyl-6-5'-cyclonucleosides, whereas those of the 2',3'-bis-O-(tert-butyldimethylsilyl derivatives underwent the C-C bond formation at the 5'-position to give (5'S)- and (5'R)-isomers. The stereochemical outcome of both types of reactions is discussed. The use of radical acceptors other than allyltributyltin was also examined.