Allyl-based groups for side-chain protection of amino-acids.

Allyl and allyloxycarbonyl groups are used for the side-chain protection of amino acids. The protecting groups may be selectively cleaved using the reagent HSnBu3 under palladium catalysis. The preparation of Boc and Fmoc series of protected amino acids is described.

[1]  F. Rutjes,et al.  Palladium-Catalyzed Reactions with N,N'-Diallyloxycarbonylhydrazines , 1991 .

[2]  P. J. Belshaw,et al.  Chlorotrimethylsilane Mediated Formation of ω-Allyl Esters of Aspartic And Glutamic Acids , 1990 .

[3]  Davidr . Evans,et al.  The oxidative macrocyclization of phenolic peptides. A biomimetic approach to the synthesis of the vancomycin family of antibiotics , 1989 .

[4]  R. B. Merrifield,et al.  An SN2 deprotection of synthetic peptides with a low concentration of hydrofluoric acid in dimethyl sulfide: evidence and application in peptide synthesis , 1983 .

[5]  Tomohiro Sato,et al.  Determination of threo and erythro configurations of 3-fluorophenylalanine for verifying stereochemical aspects of recently reported syntheses , 1981 .

[6]  D. Yamashiro,et al.  Adrenocorticotropins. 44. Total synthesis of the human hormone by the solid-phase method. , 1973, Journal of the American Chemical Society.

[7]  G. Han,et al.  9-Fluorenylmethoxycarbonyl amino-protecting group , 1972 .

[8]  J. Iyoda,et al.  Reaction of organotin oxides, alkoxides and acyloxides with organosilicon hydrides. New preparative method of organotin hydrides☆ , 1967 .

[9]  R. B. Merrifield Solid phase peptide synthesis. I. the synthesis of a tetrapeptide , 1963 .

[10]  J. D. Mcclure Synthesis of Spiroundecatrienones from 2,6-Di-t-butylquinone Methide and Butadienes , 1962 .

[11]  C. M. Stevens,et al.  Amino Acid Derivatives. I. Carboallyloxy Derivatives of α-Amino Acids1,2 , 1950 .

[12]  M. North,et al.  Non-proteinogenic amino acid synthesis: Synthesis of β,γ-unsaturated α-amino acids from asparic acid , 1989 .

[13]  F. Guibé,et al.  Selective palladium-catalyzed deprotection of the allyl and allyloxycarbonyl groups in phosphate chemistry and in the presence of propargyl and propargyloxycarbonyl groups , 1988 .

[14]  S. Sigmund,et al.  Bicyclic pyrazolidinones, a new class of antibacterial agent based on the β-lactam model , 1987 .

[15]  R. Sheppard,et al.  POLYAMIDE SUPPORTS FOR POLYPEPTIDE SYNTHESIS , 1976 .

[16]  R. A. Boissonnas,et al.  Synthèse du N-acétyl-L-séryl-L-tyrosyl-L-séryl-L-méthionyl-γ-L-glutamate de benzyle et de peptides apparentés , 1958 .