ChemInform Abstract: Synthesis of New Nucleosides by Coupling of Chloropurines with 2- and 3-Deoxy Derivatives of N-Methyl-D-ribofuranuronamide.

✍ Scribed by R. VOLPINI; E. CAMAIONI; S. VITTORI; L. BARBONI; C. LAMBERTUCCI; G. CRISTALLI

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 38 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199816226

✦ Synopsis

Synthesis of New Nucleosides by Coupling of Chloropurines with 2-and 3-Deoxy Derivatives of N-Methyl-D-ribofuranuronamide.

-Coupling of (II), obtained from commercially available 2-deoxy-D-ribose, with the chloropurine (I) affords regioselectively the nucleosides (III), whereas the β-methoxy analogue of (II) does not react. Glycosylation of (I) with the furanuronamide (IV) yields only (V). Deprotection and dechlorination leads to the desired new nucleosides. Product (VI) shows the highest affinity and selectivity for adenotin binding site vs. A 1 and A 2A adenosine receptor subtypes.