169514-23-2Relevant academic research and scientific papers
Synthesis of 3'-Deoxy-3'-C-Hydroxymethyl-aldopentopyranosyl Nucleosides and their Incorporation in Oligonucleotides. Part II.
Doboszewski, Bogdan,Winter, Hans De,Aerschot, Arthur Van,Herdewijn, Piet
, p. 12319 - 12336 (2007/10/02)
The synthesis of 3'-deoxy-3'-C-hydroxymethyl-aldopentopyranosyl nucleosides using an intramolecular radical C-C bond formation reaction is described.This method gives good results for the synthesis of thymine and adenine nucleosides, but not for cytosine and quanine nucleosides.Dependent on the configuration (β-D-erythro or α-L-threo), the conformation of the adenine nucleosides is clearly different (axial base moiety for α-D-erythro and equatorial adenine base for α-L-threo nucleosides) which could be explained by the gauche effect.Oligonucleotides built up to 2',3'-dideoxy-3'-C-hydroxymethyl-α-L-threo-pentopyranosyl adenine are able to form duplexes with oligothymidylate although with less stability than natural dsDNA.
Synthesis of the β-2',3'-unsaturated pentopyranosyl nucleosides and their 3'-hydroxymethyl congeners
Doboszewski,Blaton,Herdewijn
, p. 317 - 320 (2007/10/02)
Fusion of the glycal 3 and purines/pyrimidines without acid catalyst provides anomeric mixtures of the 2',3'-unsaturated pentopyranosyl nucleosides 4, which have been worked out to furnish the 3'-hydroxymethyl analogues, e.g. 5.
