Synthesis of novel L-phenylalanine derivatives substituted with a keto ylide as stable precursor of a vicinal tricarbonyl moiety
Novel L-phenylalanine derivatives 5 containing a vicinal tricarbonyl moiety at the para position of the phenyl ring were prepared in 4 steps starting from N(α)-Cbz-L-tyrosine benzyl ester. A 7 step reaction sequence lead to N(α)-Fmoc protected derivatives 9 with the tricarbonyl structure masked as its stable keto ylide precursor, which is suitable for solid phase peptide synthesis. The phosphoranylidene intermediates 8 were transformed to the trioxo compounds 5 with Oxone as oxidant.
Fretz, Heinz
p. 8475 - 8478
(2007/10/03)
Stereospecific synthesis of 4-carboxyphenylalanine and derivatives for use in Fmoc-based solid-phase peptide synthesis
Starting from N(α)-benzyloxycarbonyl-L-tyrosine(O-triflate) benzyl ester, we have prepared enantiomerically pure 4-carboxyphenylalanine and 4-methoxycarbonylphenylalanine derivatives using palladium (0) catalyzed carbonylation reactions. These unnatural amino acids were suitably protected and were used in solid-phase peptide synthesis using the Fmoc/t-butyl approach.
Wang, Wei,Obeyesekere, Nihal U.,McMurray, John S.
p. 6661 - 6664
(2007/10/03)
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