149666-71-7Relevant articles and documents
An improved synthesis of 3'-deoxy-3'-[18F]fluorothymidine ([18F]FLT) and the fate of the precursor, 2,3'-anhydro-5'-O-(4,4'-dimethoxytrityl)-thymidine
Cleij, M. C.,Steel, C. J.,Brady, F.,Ell, P. J.,Pike, V. W.,Luthra, S. K.
, p. S871 - S873 (2001)
The fate of the precursor, 2,3'-anhydro-5'-O-(4,4'-dimethoxytrityl)-thymidine was investigated during the synthesis of [18F]FLT with the aim of improving the radiochemical yield. This precursor was shown to undergo a rapid base catalysed elimination reaction and to be consumed within 5-10 min. The by-product was identified. Modification of the syntheis has produced between 1.85-3.70 GBq (50-199 mCi) of [18F]FLT in 60 min using an automated synthesis system.
New telluride-mediated elimination for novel synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides
Sheng, Jia,Hassan, Abdalla E. A.,Huang, Zhen
, p. 3725 - 3729 (2008/09/20)
(Chemical Equation Presented) Several 2′,3′-dideoxynucleosides (ddNs) and 2′,3′-didehydro-2′,3′-dideoxynucleosides (d4Ns) are FDA-approved anti-HIV drugs. Via conveniently synthesized 2,2′-anhydronucleosides, we have developed a novel synthesis of d4Ns by discovering and applying a new telluride-mediated elimination reaction. Our experiment results show that after substitution of 2,2′-anhydronucleosides with a telluride monoanion, a telluride intermediate is formed, and its elimination leads to formation of the olefin products (d4Ns). Our mechanistic study indicates that this telluride-assisted reaction consists of two steps: substitution (or addition) and elimination. By using dimethyl ditelluride (0.1 equiv) as the reagent, d4Ns can be synthesized with yields up to 90% via this telluride-mediated elimination. Our novel strategy has great potential to simplify synthesis of these drugs and to further reduce cost of AIDS treatment and will also facilitate development of novel d4N and ddN analogues.
