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Issue 6, 2005
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The facile preparation of primary and secondary amines via an improved Fukuyama–Mitsunobu procedure. Application to the synthesis of a lung-targeted gene delivery agent

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Abstract

An efficient modification of the Fukuyama–Mitsunobu procedure has been developed whereby primary or secondary amines can be synthesized from alkyl alcohols and the corresponding nosyl-protected/activated amine. Most importantly, the use of the DTBAD and diphenylpyridinylphosphine, as Mitsunobu reagents, generates reaction by-products that can be easily removed, providing a remarkably clean product mixture. This improved technique was implemented in the synthesis of a complex lipopeptide designed to target α9β1-integrin proteins predominant on upper airway epithelial cells.

Graphical abstract: The facile preparation of primary and secondary amines via an improved Fukuyama–Mitsunobu procedure. Application to the synthesis of a lung-targeted gene delivery agent

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Publication details

The article was received on 02 Dec 2004, accepted on 25 Jan 2005 and first published on 15 Feb 2005


Article type: Paper
DOI: 10.1039/B418168A
Citation: Org. Biomol. Chem., 2005,3, 1049-1057
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    The facile preparation of primary and secondary amines via an improved Fukuyama–Mitsunobu procedure. Application to the synthesis of a lung-targeted gene delivery agent

    C. Guisado, J. E. Waterhouse, W. S. Price, M. R. Jorgensen and A. D. Miller, Org. Biomol. Chem., 2005, 3, 1049
    DOI: 10.1039/B418168A

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