169736-08-7

Upstream product

• 162934-41-0 2',3'-Dideoxy-α-D-glycero-pent-2'-enopyranosyl-N⁴-benzoylcytosine 
• 169514-20-9 N-{1-[(2S,5S)-5-(Bromomethyl-dimethyl-silanyloxy)-5,6-dihydro-2H-pyran-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 

Downstream Products

• 169736-10-1 4-Amino-1-((2S,4R,5S)-5-hydroxy-4-hydroxymethyl-tetrahydro-pyran-2-yl)-1H-pyrimidin-2-one 

Relevant academic research and scientific papers

Synthesis of the β-2',3'-unsaturated pentopyranosyl nucleosides and their 3'-hydroxymethyl congeners

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.

Synthesis of 3'-Deoxy-3'-C-Hydroxymethyl-aldopentopyranosyl Nucleosides and their Incorporation in Oligonucleotides. Part II.

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.