126754-82-3Relevant academic research and scientific papers
Stereoselective Synthesis of 2-Azapurine 2'-Deoxy-β-D-ribonucleosides by Nucleobase-Anion Glycosylation
Kazimierczuk, Zygmunt,Seela, Frank
, p. 647 - 651 (2007/10/02)
Nucleobase-anion glycosylation of 6-(methylthio)-2-azapurine (1) with 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride (2) yields the 2'-deoxy-β-D-ribofuranosides 3-5 stereoselectively.The distribution of regioisomers is as follows: N-9 (32percent); N-2 (30percent), and N-7 (7percent) together with a minor amount of an unidentified labile glycosylation product.The anomeric configuration and the site of glycosylation have been assigned on the basis of the 1H-NOE difference spectral data in combination with gated-decoupled 13C-NMR and selective INEPT spectroscopy.The regioisomeric 6-methylthio nucleosides have been converted into 6-substituted derivatives of biological interest including 2'-deoxy-2-azaadenosine (8).Compound 8 is a substrate of adenosine deaminase.
