439828-88-3

Upstream product

• 24393-56-4 ethyl p-methoxycinnamate 
• 24393-56-4 ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 780795-86-0 (2S,3R)-3-Hydroxy-3-(4-methoxy-phenyl)-2-(toluene-4-sulfonyloxy)-propionic acid ethyl ester 
• 64-17-5 ethanol 
• 96125-49-4 methyl trans-3-(4-methoxyphenyl)glycidate 
• 159848-77-8 ethyl (2S,3R)-2,3-dihydroxy-3-(4-methoxyphenyl)propanoate 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 220736-25-4 (+)-(4S,5S)-5-(hydroxymethyl)-4-(4-methoxyphenyl)-1,3-oxazolidin-2-one 
• 780795-87-1 (2S,3S)-3-Azido-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid ethyl ester 

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 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.

Design and characterization of mechanism-based inhibitors for the tyrosine aminomutase SgTAM

The synthesis and evaluation of two classes of inhibitors for SgTAM, a 4-methylideneimidazole-5-one (MIO) containing tyrosine aminomutase, are described. A mechanism-based strategy was used to design analogs that mimic the substrate or product of the reaction and form covalent interactions with the enzyme through the MIO prosthetic group. The analogs were characterized by measuring inhibition constants and X-ray crystallographic structural analysis of the co-complexes bound to the aminomutase, SgTAM.

Highly regioselective ring opening of epoxides using NaN3: A short and efficient synthesis of (-)-cytoxazone

A convenient and efficient synthesis of 1,2-azido alcohols has been achieved by regioselective ring opening of epoxides using NaN3 and 4 ? molecular sieves in acetonitrile. The utility of this method has been demonstrated by achieving a short synthesis of (-)-cytoxazone in 48% overall yield.

Chemoenzymatic approach to optically active phenylglycidates: Resolution of bromo- and iodohydrins

Enantiomerically enriched phenylglycidates, precursors of the taxol C-13 phenylisoserine side chain and diltiazem, were prepared by kinetic resolution of anti-2-bromo-3-hydroxy- and anti-3-hydroxy-2-iodophenylpropanoates to provide enantioriched (2R,3R)- and (2S,3S)-halohydrins. The bulkiness and inflexibility of bromo and iodo groups in halohydrins have made them inaccessible to the active site of most of the lipases utilized for the hydrolysis of their acyloxy derivatives. In a set of 22 hydrolases screened herein, including native as well as commercial enzymes, only Aspergillus niger (Lipase AS, AMANO) could catalyze the hydrolysis with high enantioselectivity (E = 176). The resolved halohydrins easily underwent transformation to the corresponding (2S,3R)- and (2R,3S)-phenylglycidates.

Highly enantioselective epoxidation of α,β-unsaturated esters by chiral dioxirane

This paper describes a highly enantioselective epoxidation of α,β-unsaturated esters using the fructose-derived ketone 2 as catalyst and Oxone as oxidant. High ee's have been obtained for a number of trans and trisubstituted substrates (82-98% ee). The results described show that it is feasible for dioxiranes to effectively epoxidize electron-deficient olefins with high ee's. Copyright