84520-34-3Relevant academic research and scientific papers
An efficient synthesis of dehydroamino acids and dehydropeptides from O-Cbz and O-Eoc derivatives of serine and threonine
Ramesh, Ramapanicker,De, Kavita,Chandrasekaran, Srinivasan
, p. 10534 - 10542 (2008/02/13)
A simple and efficient method for the synthesis of dehydroamino acids from serine and threonine is reported. Various O-Cbz and O-Eoc derivatives of serine and threonine are prepared using CbzCl and EocCl, respectively, and are subjected to an anti-selective elimination on treatment with K2CO3 in DMF at 65 °C to afford dehydroalanine and dehydroamino butyric acid derivatives, respectively, in excellent yields. The high stability of these carbonate derivatives of serine and threonine allows their use in normal peptide synthesis as protected serine and threonine residues. Peptides synthesized by incorporating O-Cbz or O-Eoc derivatives undergo ready elimination under the reported conditions, to give the corresponding dehydropeptides in excellent yields. The reaction conditions are mild enough not to cause the racemization of other stereogenic centers present in the peptide.
TOTAL SYNTHESIS OF ANTITUMOR AGENT AT-125, (αS,5S)-α-AMINO-3-CHLORO-4,5-DIHYDRO-5-ISOXAZOLEACETIC ACID
Baldwin, Jack E.,Cha, Jin K.,Kruse, Lawrence I.
, p. 5241 - 5260 (2007/10/02)
A short and efficient total synthesis of racemic AT-125 and its racemic threo isomer proceeds via an intramolecular Michael cyclization of a protected α,β-dehydroglutamic acid γ-hydroxamate.Separation of diastereomers and deprotection to racemic AT-125 followed by enzymatic resolution of the N-chloroacetamide with hog-kidney acylase provides the natural αS,5S isomer.
Stereospezific Synthesis of α,β-Dehydroamino Acids from β-Hydroxy α-Amino Acid Derivatives
Somekh, Lila,Shanzer, Abraham
, p. 907 - 908 (2007/10/02)
A series of protected β-hydroxy α-amino acids have been converted stereospecifically to their dehydro derivatives by treatment with (diethylamino)sulfur trifluoride and pyridine, threo isomers giving rise to the Z derivatives and erythro isomers to the E derivatives.
