227005-69-8

Upstream product

• 98-88-4 benzoyl chloride 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 532-55-8 Benzoyl isothiocyanate 

Downstream Products

• 227005-71-2 (R,R)-N,N'-bis(1-phenylethyl)-N''-tert-butoxycarbonyl guanidine 
• 227005-70-1 (R)-N'-(tert-butoxycarbonyl)-N-(1-phenylethyl)thiourea 
• 51195-73-4 (R)-N-(1-phenylethyl)thiourea 

Relevant academic research and scientific papers

Thiourea Derivative of 2-[(1 R)-1-Aminoethyl]phenol: A Flexible Pocket-like Chiral Solvating Agent (CSA) for the Enantiodifferentiation of Amino Acid Derivatives by NMR Spectroscopy

Thiourea derivatives of 2-[(1R)-1-aminoethyl]phenol, (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol, (1R,2R)-(1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol, and (R)-1-phenylethanamine have been compared as chiral solvating agents (CSAs) for the enantiodiscrimination of derivatized amino acids using nuclear magnetic resonance (NMR) spectroscopy. Thiourea derivative, prepared by reacting 2-[(1R)-1-aminoethyl]phenol with benzoyl isothiocyanate, constitutes an effective CSA for the enantiodiscrimination of N-3,5-dinitrobenzoyl (DNB) derivatives of amino acids with free or derivatized carboxyl functions. A base additive 1,4-diazabicyclo[2.2.2]octane(DABCO)/N,N-dimethylpyridin-4-amine (DMAP)/NBu4OH) is required both to solubilize amino acid derivatives with free carboxyl groups in CDCl3 and to mediate their interaction with the chiral auxiliary to attain efficient differentiation of the NMR signals of enantiomeric substrates. For ternary systems CSA/substrate/DABCO, the chiral discrimination mechanism has been ascertained through the NMR determination of complexation stoichiometry, association constants, and stereochemical features of the diastereomeric solvates.

Chiral (η6-p-cymene)ruthenium(II) complexes containing monodentate acylthiourea ligands for efficient asymmetric transfer hydrogenation of ketones

The new chiral ligands (R)-/(S)-N-((1-phenylethyl)carbamothioyl)benzamide (L1/L2), (R)-/(S)-N-((1-phenylethyl)carbamothioyl)thiophene-2-carboxamide (L3/L4), and (R)-/(S)-N-((1-phenylethyl)carbamothioyl)furan-2-carboxamide (L5/L6) were synthesized, characterized, and used to prepare novel chiral Ru(II) complexes. The chiral Ru(II) complexes 1-6 were obtained from reactions between the chiral ligands L1-L6 and [RuCl2(p-cymene)2] 2. The complexes were characterized by analytical and spectroscopic (NMR, FT-IR, electronic) techniques. The solid-state structures of the ligands L1 and L3 and complexes 1, 4, and 6 were determined by single-crystal X-ray diffraction methods. In all of the complexes, the ligand is bound to the Ru(II) center only via the sulfur donor atom. This monodentate coordination of the acylthiourea ligands was observed for the first time with ruthenium. The Ru(II) complexes 1-6 all act as efficient catalysts for the asymmetric transfer hydrogenation of aromatic ketones in the presence of 2-propanol and KOH to produce chiral alcohols. All of the catalysts showed excellent conversions of up to 99% and enantiomeric excesses of up to 99%.

Histone deacetylase activators: N-acetylthioureas serve as highly potent and isozyme selective activators for human histone deacetylase-8 on a fluorescent substrate

We report, for the first time, that certain N-acetylthiourea derivatives serve as highly potent and isozyme selective activators for the recombinant form of human histone deacetylase-8 in the assay system containing Fluor-de-Lys as a fluorescent substrate. The experimental data reveals that such activating feature is manifested via decrease in the Km value of the enzyme's substrate and increase in the catalytic turnover rate of the enzyme.

Enantioselective synthesis of functionalized α-amino acids via a chiral guanidine catalyzed Michael addition reaction

Several chiral guanidines were evaluated as catalysts for the Michael reaction of glycine derivatives 7 with acrylic esters 8. The best result (30.4% ee) was obtained when 7b was reacted with 8b under the catalysis of guanidine 1 in THF.