111476-40-5

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 111476-31-4 2',3'-O-isopropylidene-5-phenylthiomethyluridine 
• 362-43-6 2',3'-O-isopropylideneuridine 
• 3816-77-1 2',3'-O-isopropylidene-5-hydroxymethyl-uridine 

Downstream Products

• 111476-32-5 5'-deoxy-5'-iodo-2',3'-O-isopropylidene-5-phenylthiomethyluridine 

Relevant academic research and scientific papers

SYNTHESIS OF 6,5'-cyclo-2',5'-DIDEOXYPYRIMIDINE NUCLEOSIDES ( NUCLEOSIDES AND NUCLEOTIDES. LXXII )

6,5'-cyclo-2',5'-dideoxyuridine and 6,5'-cyclo-5'-deoxythymidine, pyrimidine deoxynucleosides fixed in the anti conformation were synthesized.The key intermediate, 3'-O-acetyl-5-chloro-2',5'-dideoxy-5'-iodouridine ( 12 ), prepared from 2'-deoxyuridine, was cyclized by treatment with tributyltin hydride to the 6,5'-cyclo derivative ( 13 ), then dehydrochlorinated to furnish, after de-O-acetylation, 6,5'-cyclo-2',5'dideoxyuridine ( 14 ).For the synthesis of 6,5'-cyclothymidine, 3'-O-acetyl-2',5'-dideoxy-5'-iodo-5-phenylthiomethyluridine ( 22 ) was prepared from 2'-deoxyuridine and this compound was cyclized by treatment with tributyltin hydride to yield, after de-O-acetylation 6,5'-cyclo-5'-deoxythymidine ( 24 ).Keywords - cyclonucleoside; C-cyclouridine; 6,5'-cyclo-2',5'-dideoxyuridine; 6,5'-cyclo-5'deoxythymidine; 5-bromo-6,5'-cyclo-2',5'-dideoxyuridine; radical cyclization; tributyltin hydride; NMR; CD