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Org Lett. 2007 Nov 22;9(24):4967-70. Epub 2007 Oct 24.

High yield selective acylation of polyamines: proton as protecting group.

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1
Department of Chemistry & Biochemistry, California State University, Los Angeles, California 90032-8202, USA.

Abstract

An advance in the selective acylation of polyamines having identical or similar amine functions is reported. While nucleophilicity differences between the various amine functions are slight, the corresponding conjugate acids exhibit pKa values over a significant range. We have used proton as polyamine protecting group: the monoamine resulting from single deprotonation of a polyammonium compound has allowed for high yields of selective acylation.

PMID:
17958366
DOI:
10.1021/ol702206d
[Indexed for MEDLINE]
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