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An efficient synthesis of dehydroamino acids and dehydropeptides from O-Cbz and O-Eoc derivatives of serine and threonine

Ramesh, Ramapanicker and Kavita De, * and Chandrasekaran, Srinivasan (2007) An efficient synthesis of dehydroamino acids and dehydropeptides from O-Cbz and O-Eoc derivatives of serine and threonine. In: Tetrahedron, 63 (42). pp. 10534-10542.

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Abstract

A simple and efficient method for the synthesis of dehydroamino acids from serine and threonine is reported. Various O-Cbz and O-Eoc derivatives of serine and threonine are prepared using CbzCl and EocCl, respectively, and are subjected to an anti-selective elimination on treatment with $K_2CO_3$ in DMF at 65° C to afford dehydroalanine and dehydroamino butyric acid derivatives, respectively, in excellent yields. The high stability of these carbonate derivatives of serine and threonine allows their use in normal peptide synthesis as protected serine and threonine residues. Peptides synthesized by incorporating O-Cbz or O-Eoc derivatives undergo ready elimination under the reported conditions, to give the corresponding dehydropeptides in excellent yields. The reaction conditions are mild enough not to cause the racemization of other stereogenic centers present in the peptide.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier Ltd.
Keywords: Dehydroamino acids;Dehydropeptides;Carbonates;Peptide synthesis;Elimination reactions
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 06 Feb 2008
Last Modified: 19 Sep 2010 04:42
URI: http://eprints.iisc.ernet.in/id/eprint/12975

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