Synthesis of (purin-6-yl)methylphosphonate bases and nucleosides

✍ Scribed by Zbyněk Hasník; Radek Pohl; Michal Hocek

• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 318 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.02.167

✦ Synopsis

Three approaches to the synthesis of the title (purin-6-yl)methylphosphonates were investigated and compared. While, the Arbuzov reaction of 6-(iodomethyl)purines with triethyl phosphite did not work, Michaelis-Becker alkylation of the sodium salt of diethyl phosphonate with 6-(mesyloxymethyl)purines gave the desired products in good yields. The best method was based on Rh-or Pd-catalyzed cross-coupling reactions of 6-iodopurines with (diisopropoxyphosphorylmethyl)zinc bromide. In this way a small series of 6-(diisopropoxyphosphorylmethyl)purine bases and nucleosides was prepared in high yields.