58349-26-1Relevant academic research and scientific papers
Synthesis and properties of DNA containing cyclonucleosides
Yueh, Han,Yu, Hongchuan,Theile, Christopher S.,Pal, Ayan,Horhota, Allen,Greco, Nicholas,Christianson, Carl V.,McLaughlin, Larry W.
, p. 661 - 679 (2012/11/07)
Here, we present efficient syntheses of the R and S diastereomers of 8,5′-cyclo-2′-deoxyadenosine and 6,5′-cyclo-2′- deoxyuridine. We incorporated these interesting nucleosides into DNA to study how the cyclo linkage affects the stability of duplex formation.
SYNTHESIS OF 6,5'-cyclo-2',5'-DIDEOXYPYRIMIDINE NUCLEOSIDES ( NUCLEOSIDES AND NUCLEOTIDES. LXXII )
Suzuki, Yukari,Matsuda, Akira,Ueda, Tohru
, p. 1085 - 1092 (2007/10/02)
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
