Functionalization of Cysteine Derivatives by Unsymmetrical Disulfide Bond Formation

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作   者：

Mateusz Szymelfejnik;  Sebastian Demkowicz;  Janusz Rachon;  Dariusz Witt; 

作者机构：

80-952 Gdansk;  Narutowicza 11/12;  Poland;  Department of Organic Chemistry;  Chemical Faculty;  Gdansk University of Technology; 

关键词：

unsymmetrical disulfides;  sulfenyl bromide;  l-cystine;  l-cysteine;  thiols; 

期刊名称：

Synthesis: International Journal of Methods in Synthetic Organic Chemistry

i s s n：

0039-7881

年卷期：

2007 年 0 卷 22 期

页   码：

3528-3534

页   码：

摘   要：

We have developed a convenient method for the synthesis of unsymmetrical disulfides of l-cysteine under mild conditions in good to excellent yields. The described method is based on the straightforward preparation of 5,5-dimethyl-2-thioxo-1,3,2-dioxa???phosphorinane-2-sulfenyl bromide from readily available bis(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl) disulfide. The unsymmetrical disulfides can be obtained for l-cysteine derivatives and thiols bearing neutral, basic, or acidic functionalities.