20455-46-3

Upstream product

• 4358-87-6 (RS)-methyl mandelate 
• 39637-99-5 (S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride 
• 20445-31-2 R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid 
• 86561-27-5 methyl O-acetylmandalate 
• 21210-43-5 (S)-Methyl mandelate 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 20445-33-4 (R)-methoxytrifluoromethylphenylacetyl chloride 

Relevant academic research and scientific papers

NMR analysis of chiral alcohols and amines: Development of an environmentally benign "in tube" procedure with high efficiency and improved detection limit

A fast and efficient approach was developed for the NMR analysis of chiral alcohols and amines using readily available enantiopure MPA (α-methoxy- α-phenylacetic acid) and MTPA (α-methoxy-α- trifluoromethylphenylacetic acid) as chiral derivatizing agents. The procedure requires less than 5 min (including sample preparation time) for analysis using routine NMR hardware and allows accurate measurements for 0.01 mg of the sample of chiral compounds. Direct "in tube" analysis can be performed with high efficiency to determine enantiomeric purity and absolute configuration, as well as to monitor reactions in asymmetric synthesis and catalysis. The developed procedure is superior in terms of waste-free analysis of chiral compounds for environmentally benign applications.

Rational de novo design of NADH mimic for stereoselective reduction based on molecular orbital calculation

The methodology of rational design of NADH mimics in stereoselective reduction of carbonyl and imino groups based on molecular orbital calculation was described. The designed NADH mimics 1a and 1b were subjected to the reduction of benzoylformate and acetyliminophenylacetate. As expected from the calculations of the transition-states, the reduction with 1a proceeded with high stereoselectivity in both substrates, while 1b showed much lower chirality transfer.

Highly efficient chemo- and enantioselective enzymatic resolution of (+/-)-methyl O-acetylmandelates

Chemo- and enantioselective enzymatic hydrolysis of (+/-)-methyl O-acetylmandelates using AmanoPS has been described with very high yields and optical purity of the products.

NADH Mimics on Diacetone-D-glucose: Stereoselective Biomimetic Reduction of Benzoylformate and Interpretation of Chirality Transfer Deduced by Molecular Orbital Approach

We have prepared novel NADH mimics, in which the 1,4-dihydronicotinamide structure is connected to the diacetone-D-glucose molecule via its C-1 nitrogen, e.g. compound 1a, and 1b, and through the amide bond, e.g. compound 2-6, and analyzed their ability to stereoselective reduction of methyl benzoylformate.Although NADH mimics 1-3 and 6 turned out to be less effective in chirality transfer toward methyl benzoylformate, much higher chirality transfer was observed in the reactions with the compounds (4 and 5) possesing free hydroxyl groups at 5',6'-position of furanose.Importance of an additional intramolecular coordinating substitutent to bivalent metal ion has been demonstrated in enhancing the stereoselectivity in the reduction of benzoylformate with such NADH mimics.To materialize these observation, transition-states of the hydride transfer from 1-methyl-1,4-dihydronicotinamide to methyl benzoylformate in the presence of magnesium (II) ion were calculated by semi-empirical molecular orbital method, MNDO-PM3.Also discussed in this paper is a general chirality transfer mechanism deduced from the theoretical transition-state modeling.