N(3)-protection of thymidine with Boc for an easy synthetic access to sugar-alkylated nucleoside analogs |
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Authors: | Simeone Luca De Napoli Lorenzo Montesarchio Daniela |
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Affiliation: | Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, via Cintia, 4, I-80126 Napoli. |
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Abstract: | The use of Boc as a nucleobase-protecting group in the synthesis of sugar-modified thymidine analogs is reported. Boc was easily inserted at N(3) by a simple and high-yielding reaction and found to be stable to standard treatments for the removal of Ac and (t) BuMe(2) Si (TBDMS) groups, as well as to ZnBr(2) -mediated 4,4'-dimethoxytrityl (DMTr) deprotection. Boc Protection proved to be completely resistant to the strong basic conditions required to regioselectively achieve O-alkylation, therefore, providing synthetic access to a variety of sugar-alkylated nucleoside analogs. To demonstrate the feasibility of this approach, two 3'-O-alkylated thymidine analogs have been synthesized in high overall yields and fully characterized. |
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