N-urethane-protected amino alkyl isothiocyanates: synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides

Sureshbabu, Vommina V. ; Naik, Shankar A. ; Hemantha, H. P. ; Narendra, N. ; Das, Ushati ; Guru Row, Tayur N. (2009) N-urethane-protected amino alkyl isothiocyanates: synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides Journal of Organic Chemistry, 74 (15). pp. 5260-5266. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo900675s

Related URL: http://dx.doi.org/10.1021/jo900675s

Abstract

Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z' = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P212121.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:12094
Deposited On:10 Nov 2010 04:40
Last Modified:02 Jun 2011 11:45

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