1644308-41-7

Upstream product

• 511544-19-7 (S)-N-(3,4-dichlorobenzyl)proline 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 102-47-6 3,4-Dichlorophenylmethyl chloride 
• 719-59-5 5-chloro-2-aminobenzophenone 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 147-85-3 L-proline 

Relevant academic research and scientific papers

Synthesis of Chiral Spin-Labeled Amino Acids

Spin-labeled amino acids (SLAAs) are often used to determine intermolecular distances and conformations in proteins via double electron-electron resonance. Currently available SLAAs can be difficult to incorporate selectively and have little resemblance to natural side chains in proteins. Enantioselective synthesis of three spin-labeled l-amino acids is described, starting from readily available 2,2,6,6-tetramethyl-4-piperidinone. These SLAAs better replicate canonical residues in proteins and aim for biological incorporation via genetic incorporation or solid-phase peptide synthesis.

Michael addition reactions of chiral glycine Schiff base Ni (II)-complex with 1-(1-phenylsulfonyl)benzene

This work describes the first example of Michael addition reactions of chiral Ni (II)-complex of glycine Schiff base with 1-(1-(phenylsulfonyl)vinylsulfonyl) benzene. This approach was developed for asymmetric synthesis of 2-amino- 4,4-bis (phenylsulfonyl

SYNTHESIS OF A-AMANITIN AND ITS DERIVATIVES

The present invention relates to the chemical synthesis of α-amanitin and its derivatives. The present invention also relates to intermediate products of the α-amanitin synthesis.

Expedient Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid via Alkylation of Chiral Nucleophilic Glycine Equivalent

Here we disclose a practical asymmetric synthesis of an enantiomerically 97.8% ee pure N-Fmoc derivative of (S)-2-amino-4,4,4-trifluorobutanoic acid performed on >10 g scale of the target product. The method is based on alkylation (CF3-CH2-I) of a new generation of a chiral nucleophilic equivalent conducted at ambient temperature with an excellent stereochemical outcome. The developed protocol does not require any chromatographic separations and includes only one purification step via recrystallization of the final product.

Chemical kinetic resolution of unprotected β-substituted β-amino acids using recyclable chiral ligands

The first chemical method for resolution of N,C-unprotected β-amino acids was developed through enantioselective formation and disassembly of nickel(II) complexes under operationally convenient conditions. The specially designed chiral ligands are inexpensive and can be quantitatively recycled along with isolation of the target β-substituted-β-amino acids in good yields and excellent enantioselectivity. The method features a broad synthetic generality including β-aryl, β-heteroaryl, and β-alkyl-derived β-amino acids. The procedure is easily scaled up, and was used for the synthetically and economically advanced preparation of the anti-diabetic drug sitagliptin. The nick of time: A chemical method for resolution of unprotected β-amino acids rac-1 was developed through enantioselective formation and disassembly of nickel(II) complexes to deliver the target β-substituted β-amino acids in good yields and excellent enantioselectivity. The chiral ligands are inexpensive and can be quantitatively recycled. The procedure was used for the preparation of anti-diabetic drug sitagliptin.