370108-19-3Relevant academic research and scientific papers
Solid-phase synthesis of N(α)-benzyl-N(α)-cinnamyl lysine and glutamic acid derivatives
Connolly, Peter J.,Beers, Kimberly N.,Wetter, Steven K.,Murray, William V.
, p. 5187 - 5191 (2000)
Several variations of a solid-phase strategy for the synthesis of N(α)- benzyl-N(α)-cinnamyl lysine and glutamic acid derivatives are presented. Starting from the corresponding N(α)-Fmoc amino acids on Wang resin, reductive alkylation using nitrocinnamaldehyde or a substituted benzaldehyde was followed by nucleophilic displacement of a substituted benzyl halide or nitrocinnamyl bromide to provide resin-bound intermediates. Diversity was added by reduction of the nitro group and derivatization of the resulting aminocinnamyl moiety with a variety of acylating or sulfonylating reagents. Using an orthogonal protecting group strategy, N(ε)-Dde-protected lysine derivatives were further functionalized at the side-chain amino group prior to cleavage from resin. This method allows for the preparation of analog libraries having up to four points of diversity. (C) 2000 Elsevier Science Ltd.
