113400-36-5Relevant articles and documents
A concise asymmetric route to the bridged bicyclic tropane alkaloid ferruginine using enyne ring-closing metathesis
Aggarwal, Varinder K.,Astle, Christopher J.,Rogers-Evans, Mark
, p. 1469 - 1471 (2004)
Enyne metathesis has been used to prepare bridged azabicycles and applied in a short asymmetric synthesis of the tropane ferruginine. A Grubbs first generation catalyst proved to be superior to the second generation catalyst in the enyne metathesis reaction.
Enantiopure 5-CF3-Proline: Synthesis, Incorporation in Peptides, and Tuning of the Peptide Bond Geometry
Sanchez, Clément A.,Gadais, Charlène,Chaume, Grégory,Girard, Sylvaine,Chelain, Evelyne,Brigaud, Thierry
supporting information, p. 382 - 387 (2021/01/13)
The straightforward synthesis of enantiopure 5-(R)-and 5-(S)-trifluoromethylproline is reported. The key steps are a Ruppert-Prakash reagent addition on l-pyroglutamic esters followed by an elimination reaction and a selective reduction. The solution-phase and solid-phase incorporation of this unprotected enantiopure fluorinated amino acid in a short peptide chain was demonstrated. Compared to proline, the CF3 group provides a decrease of the trans to cis amide bond isomerization energy and an increase of the cis conformer population.
A high-quality N - tert-butoxycarbonyl - L - pyroglutamic acid benzyl ester industrial production method
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Paragraph 0022; 0025-0027; 0030-0032; 0035-0037; 0040-0041, (2019/05/16)
The invention relates to a bio-chemical technology field, in particular to a high-quality N - tert-butoxycarbonyl - L - pyroglutamic acid benzyl ester industrial production method, the raw material capture and L - pyroglutamic acid in the presence of a catalyst, with the chlorinated animal pen or bromination animal pen reaction to obtain the intermediate L - pyroglutamic acid benzyl ester; intermediate L - pyroglutamic acid benzyl ester organic phase under the catalyst condition, with the Boc anhydride reaction, to obtain the target crude N - tert-butoxycarbonyl - L - pyroglutamic acid benzyl ester; crude N - tert-butoxycarbonyl - L - pyroglutamic acid benzyl ester, in mixed crystals in the recrystallization solvent, for obtaining high-purity N - tert-butoxycarbonyl - L - pyroglutamic acid benzyl ester. Compared with the prior process, the present invention provides N - tert butoxycarbonyl - L - pyroglutamic acid benzyl ester industrial production method has the advantages of: can be efficient, stable production of the high-quality powder N - tert butoxycarbonyl - L - pyroglutamic acid benzyl ester, the purity is greater than 99.5%, a single impurities less than 0.1%.
A new class of non-C2-symmetric ligands for oxidative and redox-neutral palladium-catalyzed asymmetric allylic alkylations of 1,3-diketones
Trost, Barry M.,Donckele, Etienne J.,Thaisrivongs, David A.,Osipov, Maksim,Masters, James T.
supporting information, p. 2776 - 2784 (2015/03/04)
We report the discovery, synthesis, and application of a new class of non-C2-symmetric phosphoramidite ligands derived from pyroglutamic acid for use in both oxidative and redox-neutral palladium-catalyzed asymmetric allylic alkylations of 1,3-diketones. The resulting chiral products are typically obtained in high yield with good to excellent levels of enantioselectivity.