2272-49-3

Upstream product

• 64-17-5 ethanol 
• 6286-30-2 erythro-2,3-dibromo-3-phenylpropanoic acid 
• 127-09-3 sodium acetate 
• 100-52-7 benzaldehyde 
• 105-39-5 chloroacetic acid ethyl ester 
• 4610-69-9 (Z)-ethyl cinnamate 
• 146452-39-3 (2S,3R) ethyl 2-chloro-3-hydroxy-3-phenylpropionate 
• 146452-40-6 (2R,3R) ethyl 2-chloro-3-hydroxy-3-phenylpropionate 
• 757232-69-2 (2R,3R)-ethyl 2-bromo-3-hydroxy-3-phenylpropanoate 
• 757232-73-8 (2R,3R)-ethyl 3-hydroxy-2-iodo-3-phenylpropanoate 
• 77-76-9 2,2-dimethoxy-propane 
• 2272-55-1 ethyl trans-3-phenyl-1-oxirane-2-carboxylate 
• 623-73-4 diazoacetic acid ethyl ester 
• 4192-77-2 ethyl cinnamate 

Downstream Products

• 129939-61-3 (2S,3S)-3-Azido-2-hydroxy-3-phenyl ethyl propanoate 
• 792174-58-4 (2S,3S)-ethyl 3-amino-2-hydroxy-3-phenylpropanoate 
• 1432466-68-6 (2S,3S)-ethyl 3-amino-2-hydroxy-3-phenylpropanoate 
• 554420-01-8 (+)-(2S,3R)-N-methyl-N-(β-hydroxylphenethyl)-β-phenyl glycidic acid amide 
• 114376-13-5 (3S,4R,5R)-clausenamidone 
• 24290-27-5 (2-nitro-phenylsulfanyl)-acetic acid ethyl ester 
• 30825-24-2 2-Hydroxy-3-(2-nitro-phenylsulfanyl)-3-phenyl-propionic acid ethyl ester 
• 25957-39-5 Sodium Z-3-phenyl oxirane-2-carboxylate 
• 129939-44-2 Sodium (-)-(2R,3R)-Z-3-phenyl oxirane-2-carboxylate 
• 129939-43-1 Sodium (+)-(2S,3S)-Z-3-phenyl oxirane-2-carboxylate 
• 55325-49-0 (2RS,3SR)-3-Phenylisoserinamide 
• 27068-82-2 trans-(+/-)-2,3-dihydro-3-hydroxy-2-phenyl-1,5-benzothiazepin-4(5H)-one 
• 27068-82-2 cis-(+/-)-2,3-dihydro-3-hydroxy-2-phenyl-1,5-benzothiazepin-4(5H)-one 
• 19190-78-4 potassium cis-3-phenyloxiranecarboxylate 

Relevant academic research and scientific papers

Enantioselective bio-hydrolysis of various racemic and meso aromatic epoxides using the recombinant epoxide hydrolase Kau2

Abstract Epoxide hydrolase Kau2 overexpressed in Escherichia coli RE3 has been tested with ten different racemic and meso α,β-disubstituted aromatic epoxides. Some of the tested substrates were bi-functional, and most of them are very useful building blocks in synthetic chemistry applications. As a general trend Kau2 proved to be an extremely enantioselective biocatalyst, the diol products and remaining epoxides of the bioconversions being obtained - with two exceptions - in nearly enantiomerically pure form. Furthermore, the reaction times were usually very short (around 1 h, except when stilbene oxides were used), and the use of organic co-solvents was well tolerated, enabling very high substrate concentrations (up to 75 g/L) to be reached. Even extremely sterically demanding epoxides such as cis- and trans-stilbene oxides were transformed on a reasonable time scale. All reactions were successfully conducted on a 1 g preparative scale, generating diol- and epoxide-based chiral synthons with very high enantiomeric excesses and isolated yields close to the theoretical maximum. Thus we have here demonstrated the usefulness and versatility of lyophilized Escherichia coli cells expressing Kau2 epoxide hydrolase as a highly enantioselective biocatalyst for accessing very valuable optically pure aromatic epoxides and diols through kinetic resolution of racemates or desymmetrization of meso epoxides.

A novel enantioselective epoxide hydrolase from Agromyces mediolanus ZJB120203: Cloning, characterization and application

A new strain Agromyces mediolanus ZJB120203, capable of enantioselective epoxide hydrolase (EH) activity was isolated employing a newly established colorimetric screening and chiral GC analysis method. The partial nucleotide sequence of an epoxide hydrolase (AmEH) gene from A. mediolanus ZJB120203 was obtained by PCR using degenerate primers designed based on the conserved domains of EHs. Subsequently, an open reading frame containing 1167 bp and encoding 388 amino acids polypeptide were identified. Expression of AmEH was carried out in Escherichia coli and purification was performed by Nickel-affinity chromatography. The purified AmEH had a molecular weight of 43 kDa and showed its optimum pH and temperature at 8.0 and 35 C, respectively. Moreover, this AmEH showed broad substrates specificity toward epoxides. In this study, it is demonstrated that the AmEH could unusually catalyze the hydrolysis of (R)-ECH to produce enantiopure (S)-ECH. Enantiopure (S)-ECH could be obtained with enantiomeric excess (ee) of >99% and yield of 21.5% from 64 mM (R,S)-ECH. It is indicated that AmEH from A. mediolanus is an attractive biocatalyst for the efficient preparation of optically active ECH.

Method for Preparing Optically Pure (-)-Clausenamide Compound

Disclosed in the present invention is a method for preparing a (?)-clausenamide compound of formula (I), comprising: firstly, catalyzing the asymmetrical epoxidation of trans-cinnamate using a chiral ketone derived from fructose or a hydrate thereof as a catalyst, and then subjecting the product to transesterification, oxidation, cyclization and reduction successively to finally obtain the optically pure (?)-clausenamide compound of formula (I).

Metal-free ring-opening of epoxides with potassium trifluoroborates

The ring-opening of epoxides with potassium trifluoroborates proceeds smoothly in the presence of trifluoroacetic anhydride under metal-free conditions. The reactions are regioselective and afford a single diastereomer. Both electron-rich and electron-poor aryltrifluoroborates are tolerated.

BOROX catalysis: Self-assembled AMINO-BOROX and IMINO-BOROX chiral Bronsted acids in a five component catalyst assembly/ catalytic asymmetric aziridination

A five-component catalyst assembly/aziridination reaction is described starting from an aldehyde, an amine, ethyl diazoacetate, B(OPh)3, and a molecule of a vaulted biaryl ligand (VAPOL or VANOL). A remarkable level of chemoselectivity was observed since, while 10 different products could have resulted from various reactions between the five components, an aziridine was formed in 85% yield and 98% ee and only two other products could be detected in 3% yield. Studies reveal that the first in a sequence of three reactions is an exceedingly rapid amine-induced assembly of an AMINOBOROX chiral Bronsted acid species from VAPOL and B(OPh)3, which is followed by imine formation from the amine and aldehyde and the concomitant formation of an IMINO-BOROX chiral Bronsted acid and finally the reaction of the imine with ethyl diazoacetate mediated by the IMINO-BOROX catalyst to give aziridine-2-carboxylic esters with very high diastereo- and enantioselectivity.

3- and 4-uloses derived from N-acetyl- D -glucosamine: A unique pair of complementary organocatalysts for asymmetric epoxidation of alkenes

The 4-ulose and the 3-ulose, both derived in two steps from the α-methyl glycoside of N-acetyl-D-glucosamine (GlcNAc), act as organocatalysts in the asymmetric epoxidation of alkenes, with unprecedented complementary enantioselectivity. The best results are found with α,β-unsaturated esters as substrates, with enantiomeric ratios up to 90:10 and 11:89, respectively. Copyright

Catalytic enantioselective alkene epoxidation using novel spirocyclic N-carbethoxy-azabicyclo[3.2.1]octanones

A general synthetic route allowing access to several spirocyclic N-carbethoxy-azabicyclo[3.2.1]octanones is developed. These novel ketones efficiently catalyse alkene epoxidation using Oxone with up to 91.5% ee.

Asymmetric counteranion-directed transition-metal catalysis: Enantioselective epoxidation of alkenes with Manganese(III) salen phosphate complexes

(Figure Presented) Figure Presentation Paired up: A highly active and enantioselective ion-pair epoxidation catalyst, consisting of an achiral Mn |||-salen complex and a chiral phosphate counteranion, mediates the epoxidization of a wide range of alkenes with high yields and enantioselectivities (see scheme). The unique role of the counteranion is to stabilize an enantiomorphic conformation of the cationic Mn catalyst.

A diacetate ketone-catalyzed asymmetric epoxidation of olefins

(Chemical Equation Presented) A fructose-derived diacetate ketone has been shown to be an effective catalyst for asymmetric epoxidation. High ee values have been obtained for a variety of trans and trisubstituted olefins including electron-deficient α,β-unsaturated esters as well as certain cis olefins.

Gelozymes in organic synthesis. Part IV: Resolution of glycidate esters with crude Mung bean (Phaseolus radiatus) epoxide hydrolase immobilized in gelatin matrix

A crude extract of Mung bean meal (Phaseolus radiatus) possessing epoxide hydrolase activity immobilized in gelatin gel (gelozyme) is employed in the stereoselective epoxide ring opening of glycidate esters. Thus, ethyl trans-(±)-3-phenyl glycidate 1a and methyl trans-(±)-3-(4-methoxyphenyl) glycidate 1b gave (2S,3R)-glycidate esters (ee >99% and 45% yield) with gelatin immobilized enzyme in diisopropyl ether. The corresponding (2R,3S)-enantiomer of 1a was hydrolyzed by an epoxide hydrolase to predominantly give the anti-product, ethyl (2R,3R)-2,3-dihydroxy-3-phenylpropanoate, with a diastereomeric excess of 78% and ee 94% (40%). A small amount (5%) of racemic syn-product was also obtained as a result of the spontaneous hydrolysis. In the case of 1b, the hydrolysis product was racemic due to high reactivity of the glycidate toward water.