Synthesis of (Purin-6-yl)methylphosphonate Bases and Nucleosides

0342810 - ÚOCHB 2011 RIV GB eng J - Článek v odborném periodiku
Hasník, Zbyněk - Pohl, Radek - Hocek, Michal
Synthesis of (Purin-6-yl)methylphosphonate Bases and Nucleosides.
Tetrahedron Letters. Roč. 51, č. 18 (2010), s. 2464-2466. ISSN 0040-4039. E-ISSN 1873-3581
Grant CEP: GA MŠMT 1M0508
Výzkumný záměr: CEZ:AV0Z40550506
Klíčová slova: purines * nucleosides * phosphonates * cross-coupling
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 2.618, rok: 2010

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.
Trvalý link: http://hdl.handle.net/11104/0185437