Straightforward Synthesis of Depsiphosphonopeptides via Mannich-Type Multicomponent Condensation

Jiaxi Xu; Yuanhe Gao

doi:10.1055/s-2006-926324

PAPER

Straightforward Synthesis of Depsiphosphonopeptides via Mannich-Type Multicomponent Condensation

Jiaxi Xu*, Yuanhe Gao
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. of China
Fax: 86(10)62751708; e-Mail: jxxu@pku.edu.cn;

Abstract

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Abstract

A straightforward method for the synthesis of depsiphosphonopeptides via a Mannich-type multicomponent condensation of simple starting materials, such as benzyl carbamate, aldehydes, and 1-carbethoxyalkyl phosphorodichloridites, was developed. Compared to previous methods, our strategy provides a more efficient, convenient, and practical route for the preparation of depsiphosphonopeptides under mild reaction conditions with good yields. Such a strategy avoids the initial synthesis of 1-aminoalkylphosphonic acid or 1-aminoalkylphosphonous acid derivatives as starting materials.

Key words

depsiphosphonopeptides - Mannich reactions - multicomponent condensations - peptides - phosphonates - phosphonopeptides

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