论文信息 - A Novel Approach to the Synthesis of Threonyl- and Allothreonylglycine Derivatives. Application of a Reductive Acylation Technique to Diazopeptides

A Novel Approach to the Synthesis of Threonyl- and Allothreonylglycine Derivatives. Application of a Reductive Acylation Technique to Diazopeptides

Abstract The synthesis of (γ-aryloxythreonyl)peptide derivatives by the reductive acylation of N-(2-diazo-3-oxoalkanoyl)glycine esters recently has been described. In the present communication, we report the preparation of N-trifluoroacetyl-DL-allothreonylglycine ethyl ester and a tripeptide congener via sequences which do not require coupling of an allothreonine derivative with an amino acid or peptide ester.

N. Peet | J. Looker

[1] N. Peet,et al. REDUCTIVE ACYLATION OF THE ALIPHATIC DIAZO FUNCTION. N-(2-DIAZO-3-OXOALKANOYL)GLYCINE ESTERS AS SYNTHETIC PRECURSORS OF (Γ-(ARYLOXY)THREONYL)GLYCINE DERIVATIVES , 1977 .

[2] J. B. Hendrickson,et al. Direct introduction of the diazo function in organic synthesis , 1968 .

[3] J. Looker,et al. N-(2-Diazo-3-oxoalkanoyl)glycine esters. I. Synthesis of 4- and 5-phenoxyl derivatives and isomerization of N-(2-diazo-3-oxo-3-phenylpropanoyl)glycine ethyl ester , 1967 .

[4] F. Weygand,et al. N‐Trifluoracetyl‐aminosäuren, XIII. Serin‐ und Threonin‐Verbindungen , 1959 .

[5] M. Calvin,et al. Ethyl Thioltrifluoroacetate as an Acetylating Agent with Particular Reference to Peptide Synthesis , 1954 .

[6] F. Weygand. N-Trifluoracetylamino-säuren. II. Mitteil.† , 1954 .

[7] F. Weygand,et al. N‐Trifluoracetyl‐aminosäuren , 1952 .

[8] F. Weygand,et al. N‐Trifluoracetylaminosäuren, III. Mitteil.: Zwei neue Peptidsynthesen , 1955 .

[9] R. N. Lacey. Derivatives of acetoacetic acid. Part VII. α-Acetyltetramic acids , 1954 .