title: The assembly of beta-methylene-TAD, a metabolically stable analogue of the antitumor agent TAD, by the stepwise esterification of monodeprotected methylenebis-(phosphonate) benzyl esters under Mitsunobu conditions.
abstract: Synthesis of the metabolically stable analogue of thiazole-4-carboxamide adenine dinucleotide (beta-methylene-TAD) was achieved via the sequential monodeprotection of tetrabenzyl methylenebis(phosphonate) after two rounds of Mitsunobu esterifications with the corresponding nucleoside components, tiazofurin and adenosine.
authors.affiliation: Laboratory of Medicinal Chemistry, Division of Basic Sciences, National Cancer Institute, National Institutes of Health, Bethesda, MD 20892, USA.
authors.forename: H
authors.initials: H
authors.lastname: Ikeda
authors.forename: E
authors.initials: E
authors.lastname: Abushanab
authors.forename: V E
authors.initials: VE
authors.lastname: Marquez
mesh_terms: D000244:Adenosine Diphosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D004951:Esterification; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry; D010727:Phosphoric Diester Hydrolases / Q000737:chemistry; D013844:Thiazoles / Q000138:chemical synthesis*
chemical_list: D000970:Antineoplastic Agents; D063065:Organophosphonates; D013844:Thiazoles; C085445:beta-methylene thiazole-4-carboxamide adenine dinucleotide; D000244:Adenosine Diphosphate; D010727:Phosphoric Diester Hydrolases; C050225:thiazole-4-carboxamide-adenine dinucleotide phosphodiesterase