110270-52-5

Upstream product

• 110230-64-3 (R)-3-Acetoxy-2-benzylpropanol acetate 
• 2612-30-8 2-benzyl-1,3-propanediol 
• 108-24-7 acetic anhydride 
• 100-39-0 benzyl bromide 
• 49769-78-0 2-benzyl-malonic acid dimethyl ester 
• 607-81-8 diethyl 2-benzylmalonate 

Downstream Products

• 195056-66-7 (R)-2-(acetoxymethyl)-3-phenylpropanoic acid 
• 341926-07-6 (2S)-2-benzyl-3-[(t-butyloxycarbonyl)amino]propyl acetate 
• 913546-04-0 (R)-2-benzyl-3-((tert-butyldimethylsilyl)oxy)-propyl acetate 
• 205380-73-0 (S)-2-benzyl-3-((tert-butyldimethylsilyl)oxy)-propyl acetate 
• 123802-80-2 (R)-2-hydroxymethyl-3-phenylpropionic acid 
• 81110-73-8 N-(S-2-acetylthiomethyl-1-oxo-3-phenylpropyl)-glycine benzyl ester 
• 124815-67-4 (S)-2-acetylthiomethyl-3-phenylpropanoic acid 
• 341925-86-8 benzyl (2S)-2-benzyl-3-[(t-butyloxycarbonyl)amino]propanoate 
• 341926-08-7 (2S)-2-benzyl-3-[(t-butyloxycarbonyl)amino]propanol 
• 26250-90-8 (S)-2-[(tert-butoxycarbonylamino)methyl]-3-phenylpropanoic acid 

Relevant academic research and scientific papers

Optically active N- and C-terminal building blocks for the synthesis of peptidyl olefin peptidomimetics

Peptidyl olefin peptidomimetics serve as biologically active compounds or as intermediates for other peptidyl isosteres. The N-terminal side of the C=C bond could be easily prepared in an optically pure form from α-amino acids. Synthesis of C-terminal building blocks in an optically pure form is more challenging. We developed a chemoenzymatic stereoselective approach to such optically active C-terminal building blocks to be assembled into peptidyl olefins by a variety of reactions. They include an electrophilic aldehyde and nucleophilic sulfone, phosphonium salt, phosphonate, and diselenide. Key enzymatic hydrolysis of prochiral diesters to the corresponding hydroxy esters introduces optical activity. The sequence of the subsequent chemical reactions, either protection- hydrolysis-functionalization or functionalization-hydrolysis- protection, determines the absolute stereochemistry of the final building blocks.

Chemoenzymatic synthesis of enantiomerically enriched α-chiral 3-oxy-propionaldehydes by lipase-catalyzed kinetic resolution and desymmetrization

Enantiomerically enriched phenylalanine- and leucine aldehyde analogues have been prepared by lipase catalyzed desymmetrization or kinetic resolution of 1,3-propanediol derivatives as key steps. Observations of unusual enantioselectivity were made, and mo

Asymmetric synthesis of homoisoflavanone using lipase-catalyzed reaction

The (R)- and (S)-enantiomers of 3-benzyl-4-chromanone (homoisoflavanone) were synthesized starting with the optically active 2-benzyl-1,3-propanediol monoacetates, which were obtained via the lipase-catalyzed enantioselective reaction.

Chemo- and Enzyme-Catalyzed Reactions Revealing a Common Temperature-Dependent Dynamic Solvent Effect on Enantioselectivity

The enantiomeric ratio E of enzyme-catalyzed (Candida antarctica lipase and lipase PS) and chemocatalyzed (L-proline-based diamines) acylation reactions of 1-(naphthalen-2-yl)ethanol, 2-phenylpropanol, and 2-benzylpropane-1,3-diol is dependent on solvent and temperature. Plots of In E vs. 1/T showed the presence of inversion temperatures (Tinv). The Tinv values for the bio-catalyzed and the chemo-catalyzed reactions are fairly in agreement, and correspond as well to the TNMR values obtained by variable-temperature 13C-NMR experiments on the substrates in the same solvent of the resolution. This result demonstrates that clustering effects in the substrate solvation manage the chemical and the enzymatic enantioselectivity, and, moreover, that the solute-solvent cluster is always the real reacting species in solution for chemical as well as for enzymatic reactions.

Expanding the utility of proteases in synthesis: Broadening the substrate acceptance in non-coded amide bond formation using chemically modified mutants of subtilisin

The strategy of combined site directed mutagenesis and chemical modification creates chemically modified mutants (CMMs) with greatly broadened substrate specificities. We have previously reported that the CMMs of subtilisin Bacillus lentus (SBL) are efficient catalysts for the coupling of both L- and D-amino acids. We now report that these powerful catalysts also allow amide bond formation between a variety of non-coded carboxylic acids, including β-alanine and β-amino homologues of phenylalanine, with both L- and D-amino acid nucleophiles. As a guide to enzyme efficiency, a hydrolysis assay indicating pH change has been employed. CMMs selected by this screen furnished higher yields of coupling products compared to the wild-type enzyme (WT). Furthermore, both WT and CMM enzymes allow highly stereoselective aminolysis of a meso diester with an amino acid amine. These results highlight the utility of CMMs in the efficient formation of non-coded amides as potential peptide isosteres.

New asymmetric synthesis of dexecadotril and ecadotril starting from a single precursor

We describe herein a method providing access to both enantiomers of 3-acetylthio-2-benzylpropionic acid via enzymatic desymmetrization of 2-benzyl-1,3-propanediol. These compounds are respectively the starting materials for the synthesis of ecadotril, and dexecadotril, which are powerful inhibitors of NEP (EC 3.4.24.11) and have been developed as therapeutic agents.

Lipase-based HPLC stationary phase: Enantioselective synthesis of 2- substituted 1,3-propanediol monoacetates

Pseudomonas cepacia lipase (PCL) has been immobilized by coating the enzyme on an epoxysilica HPLC column. The biocatalyst has been successfully used for the preparation of both the enantiomers of 3-acetoxy-2-benzyl- propan-1-ol and of 3-acetoxy-2-methylpropan-1-ol. The immobilized enzyme is active after months of use either in aqueous or in organic media. (C) 1999 Elsevier Science Ltd.

Prediction of the solvent dependence of enzymatic prochiral selectivity by means of structure-based thermodynamic calculations

A new, quantitative model is elaborated to rationalize the solvent dependence of enzymatic selectivity solely on the basis of the thermodynamics of substrate solvation. The model predicts that any type of the selectivity (defined as the ratio of k(cat)/K(

N-substituted acylamino acid compounds, process for their production and their use

The present invention provides an N-substituted acylamino acid compound of the formula: STR1 a process for their production and pharmaceutical uses, and intermediates useful for their production.