Tetrahedron letters2022，Vol.956.DOI:10.1016/j.tetlet.2022.153728

Stereoselective synthesis of 2-deoxy-2-disubstituted ribonolactones through a TiCl4-mediated Evans-Aldol reaction

Liu, He Yang, Wenjiao Zheng, Shaojiu He, Yang Wang, Guan Qin, Hongjian Zhu, Fuqiang Jiang, Xiangrui Shen, Jingshan Gong, Xudong
Tetrahedron letters2022，Vol.956.DOI:10.1016/j.tetlet.2022.153728
✕
  • NSTL
  • Elsevier

Stereoselective synthesis of 2-deoxy-2-disubstituted ribonolactones through a TiCl4-mediated Evans-Aldol reaction

Liu, He 1Yang, Wenjiao 2Zheng, Shaojiu 2He, Yang 2Wang, Guan 2Qin, Hongjian 2Zhu, Fuqiang 3Jiang, Xiangrui 2Shen, Jingshan 2Gong, Xudong3
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作者信息

  • 1. Univ Sci & Technol China
  • 2. Chinese Acad Sci
  • 3. Topharman Shanghai Co Ltd
  • 折叠

Abstract

A convenient and novel route for the stereoselective synthesis of 3,5-Di-O-benzoyl-2-deoxy-2-chloro-2-C-methyl-D-ribono-c-lactone 5a and its analogues is developed by an Evans-Aldol reaction in the presence of TiCl4. Starting from 2-chloropropionyl chloride, 5a is efficiently and regioselectively produced on a kilogram scale in an overall yield of 32% with an HPLC purity of 98% by area. In addition, this approach allowed an efficient synthesis of 3,5-Di-O-benzoyl-2-deoxy-2-fluoro-2-C-methyl-D-ribono-c- lactone 5b in a total 20% yield. (C)& nbsp;2022 Elsevier Ltd. All rights reserved.

Key words

Asymmetric synthesis/Stereoselectivity/Ribonolactone/Evans-Aldol reaction/CHIRAL AUXILIARIES/NUCLEOSIDE/ADDITIONS/OXAZOLIDINONES/POLYMERASE/DISCOVERY/PRODRUGS

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出版年

2022
Tetrahedron letters

Tetrahedron letters

CCR
ISSN：0040-4039
参考文献量31
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