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

[Display omitted] A convenient and novel route for the stereoselective synthesis of 3,5-Di-O-benzoyl-2-deoxy-2-chloro-2-C-methyl-ᴅ-ribono-γ-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 r...

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Published inTetrahedron letters Vol. 95; pp. 153728 - 153733
Main Authors Liu, He, Yang, Wenjiao, Zheng, Shaojiu, He, Yang, Wang, Guan, Qin, Hongjian, Zhu, Fuqiang, Jiang, Xiangrui, Shen, Jingshan, Gong, Xudong
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 13.04.2022
Elsevier
Subjects
Asymmetric synthesis
Chemistry
Chemistry, Organic
Evans-Aldol reaction
Physical Sciences
Ribonolactone
Science & Technology
Stereoselectivity
Stereoselectivity
Asymmetric synthesis
Evans-Aldol reaction
Ribonolactone
NUCLEOSIDE
PRODRUGS
CHIRAL AUXILIARIES
POLYMERASE
OXAZOLIDINONES
ADDITIONS
DISCOVERY
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Summary:[Display omitted] A convenient and novel route for the stereoselective synthesis of 3,5-Di-O-benzoyl-2-deoxy-2-chloro-2-C-methyl-ᴅ-ribono-γ-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-ᴅ-ribono-γ-lactone 5b in a total 20% yield.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.153728