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Simple and efficient synthesis of allo- and threo-3,3'-dimiethylcystine derivatives in enantiomerically pure form

Baig, Nasir RB and Sudhir, Sai V and Chandrasekaran, Srinivasan (2008) Simple and efficient synthesis of allo- and threo-3,3'-dimiethylcystine derivatives in enantiomerically pure form. In: Tetrahedron: Asymmetry, 19 (12). pp. 1425-1429.

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Abstract

A simple and efficient method for the synthesis of allo- and threo-3,3'-dimethylcystine derivatives is reported. Various tosyl and bromo derivatives of Cbz-, Boc-, and Fmoc-protected threonine methyl esters have been prepared and subjected to nucleophilic substitution with potassium thiocyanate in acetonitrile to yield the corresponding thiocyanate derivatives in moderate yield. The thiocyanates are readily converted to the corresponding allo- and threo-3,3'-dimethylcystine derivatives via reductive dimerization with benzyltriethylammonium tetrathiomolybdate.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 04 Sep 2008 05:54
Last Modified: 19 Sep 2010 04:49
URI: http://eprints.iisc.ernet.in/id/eprint/15679

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