87363-79-9Relevant academic research and scientific papers
Novel stereospecific dehydration of β-hydroxy-α-amino acids using Martin's sulfurane
Yokokawa, Fumiaki,Shioiri, Takayuki
, p. 8679 - 8682 (2002)
The stereospecific dehydration of threo-N-acyl-β-hydroxy-α-amino acid derivatives was performed using Martin's sulfurane to give (Z)-α,β-dehydroamino acids, while erythro-N-acyl-β-hydroxy-α-amino acid amides were converted to 4,5-trans-oxazolines using an
An improved procedure for the synthesis of dehydroamino acids and dehydropeptides from the carbonate derivatives of serine and threonine using tetrabutylammonium fluoride
Ramapanicker, Ramesh,Mishra, Roli,Chandrasekaran, Srinivasan
experimental part, p. 123 - 125 (2011/02/24)
Dehydroamino acids are important precursors for the synthesis of a number of unnatural amino acids and are structural components in many biologically active peptide derivatives. However, efficient synthetic procedures for their production in large amounts
(DIETHYLAMINO)SULFUR TRIFLUORIDE (DAST) AS A USEFUL REAGENT FOR THE PREPARATION OF 2-OXAZOLINES FROM 1,2-AMIDO ALCOHOLS
Lafargue, Pierre,Guenot, Pierre,Lellouche, Jean-Paul
, p. 947 - 958 (2007/10/02)
Acylic 1,2-amido alcohols (6) react efficiently with a slight excess of (diethylamino)sulfur trifluoride (DAST) to afford the corresponding 2-oxazolines (10) in good yields ranging between 57-95percent.Even at the low temperature of -78 deg C, a rapid ( 1 h) and stereoselective amide cyclization is observed without formation of acylaziridine by-products.The scope of this cyclization is discussed.
Dehydrooligopeptides. VII. Convenient Synthesis of Various Dehydrodi- and tripeptide Esters by Using N-Carboxy α-Dehydroamino Acid Anhydride
Shin, Chuung-gi,Yonezawa, Yasuchika,Ikeda, Masahiro
, p. 3573 - 3579 (2007/10/02)
The one-pot syntheses of N-protected Δ1- and Δ2-dehydrodipeptide esters by the coupling of N-carboxy α-dehydroamino acid anhydride (ΔNCA) with several kinds of C- or N-protected L-α-amino acids are described.In addition, it was found that a similar coupling of ΔNCA with both C- and N-protected α-amino acids also took place to give Δ2-dehydrotripeptide derivatives, involving eight kinds of important C-terminal segments of antrimycins and cirratiomycins.The configurational confirmation of the α-dehydroisoleucine residue of the antibiotics is also discussed.
