Synthesis of 2'beta-Deoxy-[8-(13)C;amino,9-(15)N(2)]adenosine: Unusual Annulation Conditions To Assemble the Purine Core

Charles C. Orji; Ryszard Michalczyk; Louis A. "Pete Silks III

doi:10.1021/jo9824753

Synthesis of 2'beta-Deoxy-[8-(13)C;amino,9-(15)N(2)]adenosine: Unusual Annulation Conditions To Assemble the Purine Core

J Org Chem. 1999 Jun 25;64(13):4685-4689. doi: 10.1021/jo9824753.

Authors

Charles C. Orji¹, Ryszard Michalczyk, Louis A. "Pete Silks III

Affiliation

¹ Los Alamos National Laboratory, Chemical Sciences and Technology Division, CST-4, The Bioscience and Biotechnology Group, MS; E529, Los Alamos, New Mexico 87545.

PMID: 11674540
DOI: 10.1021/jo9824753

Abstract

Synthesis of 2'beta-Deoxy-[8-(13)C;amino,9-(15)N(2)]adenosine has been accomplished using a five-step process which employs a novel annulation of [(13)C]formamide [N-(4-[(15)N]amino-6-chloro-5-pyrimidinyl)] 2. To effect this dehydration, a complex of triethyl phosphite and TiCl(2)(i-OPr)(2) was used. 6-Chloro-[8-(13)C; 9-(15)N]purine was then converted in two steps to 2'beta-deoxy-[8-(13)C;amino,9-(15)N(2)]adenosine.