51163-40-7Relevant articles and documents
Constrained Cyclic β,γ-Diamino Acids from Glutamic Acid: Synthesis of Both Diastereomers and Unexpected Kinetic Resolution
Wan, Yang,Auberger, Nicolas,Thétiot-Laurent, Sophie,Bouillère, Francelin,Zulauf, Ana?s,He, Jiefang,Courtiol-Legourd, Stéphanie,Guillot, Régis,Kouklovsky, Cyrille,Cote des Combes, Sylvain,Pacaud, Christophe,Devillers, Ingrid,Alezra, Valérie
, p. 329 - 340 (2018/01/27)
We describe here an efficient synthesis of both diastereomers of cyclic β,γ-diamino acids starting from l-glutamic acid, based on the Blaise reaction. We show that by changing the protecting group, we can access either the five-membered-ring lactam, which
'BOP' as a reagent for mild and efficient preparation of esters
Kim,Patel
, p. 5603 - 5606 (2007/10/02)
A simple procedure for preparation of esters under mild conditions employing the BOP reagent is reported. Acid and base labile protecting groups commonly used with amino acids e.g. t-butyl, Fmoc etc., are well tolerated under these conditions. The mechani
Synthesis of the Dolastatin Thiazole Amino Acid Component (gln)Thz
Holzapfel, Cedric W.,Pettit, George R.
, p. 2323 - 2327 (2007/10/02)
The new thiazole amino acid (gln)Thz, found to occur as one unit of the marine sea hare cyclic pentapeptide dolastin 3, has been synthesized from L-glutamic acid by the route 2 -> 10e.The synthesis of Z-L-isoglutamine (4) was improved by selective ammonolysis of anhydride 3 at -60 deg C.A variety of reaction conditions were found to cause complete racemization during the Hantzsch thiazole synthesis step (9 -> 10).Deuterium labeling experiments indicated loss of the chiral center prior to formation of the thiazole system and suggested an imine-enamine type equilibration involving intermediates A B (Scheme II).The N-benzyloxycarbonyl derivative (10d) of (gln)Thz was partially resolved by employing brucine.