153547-60-5

Upstream product

• 95-57-8 2-monochlorophenol 
• 57044-25-4 (R)-oxiranemethanol 
• 2212-04-6 1-(2-chlorophenoxy)-2,3-epoxypropane 
• 206259-32-7 (4R,5R)-2-chloro-N,N,N',N'-tetramethyl-1,3,2-dioxaphospholane-4,5-dicarboxamide 
• 147220-29-9 1-acetoxy-3-(2-chlorophenoxy)propan-2-ol 
• 5112-21-0 rac-3-(2-chlorophenoxy)propane-1,2-diol 
• 204584-21-4 1-acetoxy-3-(2-chlorophenoxy)propan-2-one 
• 147220-39-1 Acetic acid (S)-1-acetoxymethyl-2-(2-chloro-phenoxy)-ethyl ester 

Downstream Products

• 128994-26-3 (R)-(-)-1-(2-chlorophenoxy)-2,3-epoxypropane 

Relevant academic research and scientific papers

Bacillus alcalophilus MTCC10234 catalyzed enantioselective kinetic resolution of aryl glycidyl ethers

The phenyl glycidyl ether derivatives have been kinetically resolved with the growing cells of Bacillus alcalophilus MTCC10234 yielding (S)-epoxides with up to >99% ee and (R)-diols with up to 89% ee. The enantiomeric ratio (E) of up to 67 has been obtained for biohydrolysis process. The effect of different substituents of phenyl glycidyl ether on the biocatalytic efficiency of B. alcalophilus MTCC10234 showed preference for methyl- and chloro-substituted aryl glycidyl ether derivatives whereas nitro-derivatives were transformed at a slower rate. 2,6-Dimethylphenyl glycidyl ether which contains a bulky aryl group having methyl group on both the ortho positions was resolved with an E=39.

Crystallization of chiral compounds 3. 3-Phenoxypropane-1,2-diol and 3-(2-halophenoxy)propane-1,2-diols

Specific features of melting of crystalline samples of 3-(2-R-phenoxy) propane-1,2-diols with different enantiomeric compositions were studied by differential scanning calorimetry. The melting points and enthalpies of melting for the racemate and individual stereoisomers were determined. Binary phase diagrams were constructed. The entropy of mixing of individual enantiomers in the liquid phase and the free energy of formation of the racemic compound were calculated. The thermochemical data indicate that the racemates are formed upon the crystallization of phenoxy-and 2-fluorophenoxy-containing compounds, while crystallization of the chloro-, bromo-, and iodo-substituted analogs would form racemic conglomerates.

Jacobsen-type enantioselective hydrolysis of aryl glycidyl ethers. 31P NMR analysis of the enantiomeric composition of oxiranes

The enantioselective partial hydrolysis of a number of racemic aryl glycidyl ethers in the presence of chiral Co(salen)-catalyst was studied. The enantiomeric composition of the isolated (R)-aryl glycidyl ethers was analyzed by 31P NMR using optically active substituted 2-chloro-1,3,2- dioxaphospholanes. A synthesis of β-adrenoblocking agents (S)-toliprolol and (S)-moprolol based on the simultaneously obtained (S)-3-aryloxypropane-1,2- diols was proposed.

Baker's yeast mediated stereoselective biotransformation of 1-acetoxy-3-aryloxypropan-2-ones

A series of 1-acetoxy-3-aryloxypropan-2-ones 1a-m were synthesized and subjected to biotransformation by baker's yeast yielding optically active monoacetates 5 or ent-5 and/or diols 4 of moderate to excellent enantiomeric purity. The dependence of the reduction/hydrolysis ratio and stereoselectivity on the size and substitution pattern of the aromatic moiety in the substrate is also discussed.

Studies on agents with vasodilator and β-blocking activities. III synthesis and activity of optical isomers of TZC-1370

Optical isomers of TZC-1370 (1) were prepared from (R)- and (S)-1-(2- chlorophenoxy)-2,3-epoxypropane. When given intravenously to anesthetized rats, the (S)-isomer was about 40 times more potent in terms of β-blocking activity than the (R)-isomer, while

A Practical Synthetic Route to Enantiopure 3-Aryloxy-1,2-propanediols from Chiral Glycidol

Chiral 3-aryloxy-1,2-propanediols of >98percent ee can be obtained in high yield by the nucleophilic addition of substituted phenols to chiral glycidol in the presence of triethylamine catalyst followed by recrystallization in absolute ethanol.Several enantiopure compounds of pharmaceutical significance are presented as examples.

Kinetic resolution of acyclic 1,2-diols using a sequential lipase- catalyzed transesterification in organic solvents

A method for the kinetic resolution of 3-(aryloxy)-1,2-propanediols rac- 1a-n without additional protection-deprotection steps using a lipase- catalyzed sequential transesterification with lipase amano PS has been developed. In the first step of this one-pot procedure the racemic 1,2-diols are acylated regioselectively at the primary hydroxy group without enantioselection. The subsequent acylation at the secondary hydroxy group of the formed primary monoacetate is responsible for high enantioselection. The enantioselectivity of this transformation depends significantly on the substitution pattern of the aryl ring and the organic solvent used. 3- (Aryloxy)-1,2-propanediols with substituents in the para-position show a much higher enantioselectivity than the corresponding derivatives with ortho- substituents. Among other substrates, the pharmaceuticals Mephenesin, Guaifenesin, and Chlorphenesin have been resolved. The replacement of the aryloxy by an alkyl substituent causes a dramatic decrease of enantioselectivity.