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

Baig, Nasir Rashid Baig and Chandrakala, RN and Sudhir, Sai V and Chandrasekaran, Srinivasan (2010) Synthesis of Unnatural Selenocystines and beta-Aminodiselenides via Regioselective Ring-Opening of Sulfamidates Using a Sequential, One-Pot, Multistep Strategy. In: Journal of Organic Chemistry, 75 (9). pp. 2910-2921.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo1001388

Abstract

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.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 26 May 2010 07:25
Last Modified: 19 Sep 2010 06:07
URI: http://eprints.iisc.ernet.in/id/eprint/28049

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