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.
H Ikeda, E Abushanab, V E Marquez
Laboratory of Medicinal Chemistry, Division of Basic Sciences, National Cancer Institute, National Institutes of Health, Bethesda, MD 20892, USA.
Bioorganic & medicinal chemistry letters 1999 Nov 1Synthesis 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.
Citation
H Ikeda, E Abushanab, V E Marquez. 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. Bioorganic & medicinal chemistry letters. 1999 Nov 1;9(21):3069-74
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PMID: 10560727
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