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Abstract <p>A preparative procedure has been developed for the synthesis of 3′-<i>O</i>-{[2-(2-nitrophenyl)propoxy]carbonyl}thymidine 5′-phosphoramidite, the key reagent for the photolithographic synthesis of oligonucleotides on a solid support. The synthetic steps, including the preparation of 2-(2-nitrophenyl)propyl chloroformate, have been considered in detail, and conditions for the removal of the trityl protecting group from 3′-<i>O</i>-(2-(2-nitrophenyl)propoxycarbonyl)-5′-<i>O</i>-tritylthymidine have been optimized. The UV spectral properties of 3′-<i>O</i>-{[2-(2-nitrophenyl)propoxy]carbonyl}thymidine 5′-phosphoramidite have been studied, its molar absorption coefficient has been refined, and the results have been compared with the previously reported data for 2-(2-nitrophenyl)propan-1-ol.</p>

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Synthesis and Spectral Properties of 3′-O-NPPOC-Thymidine 5′-Phosphoramidite

  • 期刊论文

  • 发表日期：

    2026年2月1日

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  • D. A. Kazantsev,
  • A. A. Denisov,
  • M. S. Valova,
  • A. V. Pestov

摘要

Abstract

A preparative procedure has been developed for the synthesis of 3′-O-{[2-(2-nitrophenyl)propoxy]carbonyl}thymidine 5′-phosphoramidite, the key reagent for the photolithographic synthesis of oligonucleotides on a solid support. The synthetic steps, including the preparation of 2-(2-nitrophenyl)propyl chloroformate, have been considered in detail, and conditions for the removal of the trityl protecting group from 3′-O-(2-(2-nitrophenyl)propoxycarbonyl)-5′-O-tritylthymidine have been optimized. The UV spectral properties of 3′-O-{[2-(2-nitrophenyl)propoxy]carbonyl}thymidine 5′-phosphoramidite have been studied, its molar absorption coefficient has been refined, and the results have been compared with the previously reported data for 2-(2-nitrophenyl)propan-1-ol.