Synthesis of Unnatural Selenocystines and β-Aminodiselenides via Regioselective Ring-Opening of Sulfamidates Using a Sequential, One-Pot, Multistep Strategy

被引：40

作者：

Baig, Nasir Rashid Baig ^{[2
]}

Chandrakala, R. N. ^{[2
]}

Sudhir, V. Sai ^{[2
]}

Chandrasekaran, Srinivasan ^{[1
]}

机构：

[1] Indian Inst Sci, Jawaharlal Nehru Ctr Adv Sci Res, Bangalore 560012, Karnataka, India

[2] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 09期

关键词：

DIFERROCENYL DICHALCOGENIDES; THIOREDOXIN REDUCTASE; DIETHYLZINC ADDITION; EFFICIENT SYNTHESIS; SELENATING REAGENT; CHIRAL DISELENIDES; AMINO DISELENIDES; SELENIUM; TETRATHIOMOLYBDATE; ORGANOSELENIUM;

D O I：

10.1021/jo1001388

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of N-alkyl-beta-aminodiselenides have been synthesized in high yield from sulfamidates under mild reaction conditions using potassium selenocyanate and benzyltriethylammonium tetrathiomolybdate ([BnNEt3](2)MoS4) in a sequential, one-pot, multistep reaction. The tolerance of multifarious protecting groups under the reaction conditions is discussed. The methodology was successfully extended to the synthesis of selenocystine, 3,3'-dialkylselenocystine, and 3,3'-diphenylisoselenocystine and their direct incorporation into peptides.

引用

页码：2910 / 2921

页数：12

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