Synthesis of unnatural selenocystines and beta-aminodiselenides via regioselective ring-opening of sulfamidates using a sequential, one-pot, multistep strategy.

Nasir Baig Rashid Baig, R N Chandrakala, V Sai Sudhir, Srinivasan Chandrasekaran

Index: J. Org. Chem. 75(9) , 2910-21, (2010)

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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 ([BnNEt(3)](2)MoS(4)) 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.