170638-72-9Relevant academic research and scientific papers
3'-C-hydroxymethylthymidine: Synthesis and incorporation into oligodeoxynucleotide analogues
Jorgensen,Svendsen,Nielsen,Wengel
, p. 921 - 924 (1995)
The stereoselective synthesis of 3'-C-hydroxymethylthymidine (5) in five steps from thymidine has been accomplished and this nucleoside has been incorporated into oligodeoxynucleotides (ODNs) in different ways.
Synthesis of novel 3'-C-(hydroxymethyl)thymidines and oligodeoxynucleotide analogues containing compressed 3'-C-hydroxymethyl-linked phosphodiester backbones
Wengel,Svendsen,Jorgensen,Nielsen
, p. 1465 - 1479 (1995)
Lombardo methylenation of the novel 2'-deoxy-3'-ketonucleosides 4 afforded 2',3'-dideoxy-3'-C-methylene nucleosides 5, which were subjected to catalytic dihydroxylation reactions. In the case of 5'-deoxynucleoside 5a, a 1:1 mixture of 3'-C-hydroxymethyl diastereoisomers 6a and 7a was obtained, whereas the 5'-O-silylated nucleoside 5b afforded 3'-C- (hydroxymethyl)thymidine derivative 6b as the only product. Sharpless asymmetric dihydroxylation of 5a proceeded in low yield to give 6a and 7a as a 10:3 mixture. 5'-O-Silylated nucleoside 6b was converted into the phosphoramidite synthon 9, which was applied in automated syntheses of oligodeoxynucleotides containing novel compressed 3'-C-hydroxymethyl linked phosphodiester backbones.
