101693-40-7

Basic information

• Product Name: Oxirane, [(4-methylphenoxy)methyl]-, (S)-
• Synonyms: (S)-1,2-epoxy-3-(4-methylphenoxy)propane;(S)-glycidyl p-methylphenyl ether;(S)-glycidyl 4-methylphenyl ether;(S)-glycidyl-4-methylphenyl ether;(2S)-(+)-3-[4'-methylphenoxy]-1,2-epoxypropane;(S)-2,3-epoxypropyl p-tolyl ether
• CAS NO: 101693-40-7
• Molecular Formula: C10H12O2
• Molecular Weight: 164.204
• Mol File: 101693-40-7.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Oxirane, [(4-methylphenoxy)methyl]-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxirane, [(4-methylphenoxy)methyl]-, (S)-(101693-40-7)
• EPA Substance Registry System: Oxirane, [(4-methylphenoxy)methyl]-, (S)-(101693-40-7)

Safety Data

• Hazardous Substances Data: 101693-40-7(Hazardous Substances Data)

Upstream product

• 106-44-5 p-cresol 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 2186-24-5 cresyl-glicidyl ether 
• 115314-14-2 (2s)-(+)-glycidyl 3-nitrobenzenesulfonate 
• 118712-60-0 S-oxiran-2-ylmethyl 4-nitrobenzenesulfonate 
• 70987-78-9 (S)-Glycidyl tosylate 

Downstream Products

• 1349343-07-2 1-(2-(N-(9-anthracenylmethyl)-N-((2S)-2-hydroxy-3-(4'-methyl)phenoxypropyl)amino)ethyl)-4,7,10-tris((2S)-2-hydroxy-3-(4'-methyl)phenoxypropyl)-1,4,7,10-tetraazacyclododecane 
• 1078732-32-7 1-(benzyloxycarbonyl)-4,7,10-tris((2S)-2-hydroxy-3-[4'-(methyl)phenoxy]propyl)-1,4,7,10-tetraazacyclododecane 

Relevant articles and documents

CsF in organic synthesis. The first and convenient synthesis of enantiopure bisoprolol by use of glycidyl nosylate

The regioselective substitution of glycidyl nosylate with phenols is catalyzed by CsF in the presence of K2CO3 in DMF; this reaction enables the first and convenient synthesis of enantiopure bisoprolol.

Improving the activity and enantioselectivity of PvEH1, a Phaseolus vulgaris epoxide hydrolase, for o-methylphenyl glycidyl ether by multiple site-directed mutagenesis on the basis of rational design

Substrate spectrum assay exhibited that PvEH1, which is an epoxide hydrolase from P. vulgaris, had the highest specific activity and enantiomeric ratio (E) for racemic o-methylphenyl glycidyl ether (rac-1) among tested aryl glycidyl ethers (1–5). To produce (R)-1 via kinetic resolution of rac-1 efficiently, the catalytic properties of PvEH1 were further improved on the basis of rational design. Firstly, the seven single-site variants of PvEH1-encoding gene (pveh1) were PCR-amplified as designed, and expressed in E. coli BL21(DE3). Among all expressed single-site mutants, PvEH1L105I and PvEH1V106I had the highest specific activities of 17.6 and 16.4 U/mg protein, respectively, while PvEH1L196D had an enhanced E value of 9.2. Secondly, to combine their respective merits, one triple-site variant, pveh1L105I/V106I/L196D, was also amplified, and expressed. The specific activity, E value, and catalytic efficiency of PvEH1L105I/V106I/L196D were 23.1 U/mg, 10.9, and 6.65 mM?1 s?1, respectively, which were 2.0-, 1.8- and 2.4-fold higher than those of wild-type PvEH1. The source of PvEH1L105I/V106I/L196D with enhanced E value for rac-1 was preliminarily analyzed by molecular docking simulation. Finally, the scale-up kinetic resolution of 100 mM rac-1 was conducted using 5 mg wet cells/mL E. coli/pveh1L105I/V106I/L196D at 25 °C for 1.5 h, producing (R)-1 with 95.0% ees, 32.1% yield and 3.52 g/L/h space-time yield.

Chiral nanoporous metal-metallosalen frameworks for hydrolytic kinetic resolution of epoxides

Chiral nanoporous metal-organic frameworks are constructed by using dicarboxyl-functionalized chiral Ni(salen) and Co(salen) ligands. The Co(salen)-based framework is shown to be an efficient and recyclable heterogeneous catalyst for hydrolytic kinetic resolution (HKR) of racemic epoxides with up to 99.5% ee. The MOF structure brings Co(salen) units into a highly dense arrangement and close proximity that enhances bimetallic cooperative interactions, leading to improved catalytic activity and enantioselectivity in HKR compared with its homogeneous analogues, especially at low catalyst/substrate ratios.