61393-94-0

Usage

Uses

Used in Organic Synthesis:
(2S)-2-benzyloxirane is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, contributing to the production of a range of pharmaceuticals, agrochemicals, and other industrial products.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (2S)-2-benzyloxirane is utilized as a building block in the synthesis of complex organic molecules, playing a crucial role in the development of new drugs and medicinal compounds.
Used in Agrochemical Production:
Similarly, in agrochemical manufacturing, (2S)-2-benzyloxirane serves as a key intermediate in the synthesis of various agrochemicals, helping to create effective products for agricultural applications.
Used in Industrial Product Development:
Beyond pharmaceuticals and agrochemicals, (2S)-2-benzyloxirane is also employed in the development of other industrial products, capitalizing on its reactivity and structural properties to enhance the creation of diverse chemical compounds and materials.

Upstream product

• 27720-03-2 S-2-(Dimethylamino)-3-phenyl-1-propanol 
• 219500-45-5 (-)-(S)-2-bromo-3-phenylpropan-1-ol 
• 4436-24-2 1,2-epoxy-3-phenylpropane 
• 51-79-6 urethane 
• 155498-78-5 Toluene-4-sulfonic acid (R)-2-hydroxy-3-phenyl-propyl ester 
• 937-38-2 1-chloro-3-phenylpropan-2-one 
• 67-56-1 methanol 
• 828-01-3 D-phenyllactic acid 
• 122-78-1 phenylacetaldehyde 
• 7474-06-8 (S)-2-chloro-3-phenyl-propionic acid 
• 63-91-2 L-phenylalanine 
• 91465-27-9 N,N-dimethyl-L-phenylalanine ethyl ester 
• 3081-24-1 H-Phe-OEt 
• 591-51-5 phenyllithium 

Downstream Products

• 127102-59-4 (2R,12R)-1,13-diphenyl-4,7,10-trioxatridecane-2,12-diol 
• 1517-68-6 (S)-1-phenylpropan-2-ol 
• 156-34-3 l-amphetamine 
• 2323-36-6 SELEGILINE 
• 33817-09-3 (R)-2-methylamino-1-phenylpropane 
• 167421-83-2 tert-butyl N-[(1R)-1-methyl-2-phenylethyl]carbamate 
• 863482-65-9 1-((R)-2-azidopropyl)benzene 
• 127102-53-8 (4R,14R)-4,14-dibenzyl-3,6,9,12,15-pentaoxa-21-azabicyclo<15.3.1>heneicosa-1(21),17,19-triene 
• 1026798-68-4 (R)-1-[(3S,6S)-6-benzhydrylpiperidin-3-ylamino]-3-phenylpropan-2-ol 
• 1187560-41-3 C₁₆H₂₂O₂ 
• 1187560-42-4 C₁₅H₁₆OS 
• 1222139-32-3 1-(3-bromophenyl)-3-phenyl-2(R)-propanol 
• 17131-14-5 (R)-3-phenylpropane-1,2-diol 

Relevant academic research and scientific papers

Asymmetric azidohydroxylation of styrene derivatives mediated by a biomimetic styrene monooxygenase enzymatic cascade

Enantioenriched azido alcohols are precursors for valuable chiral aziridines and 1,2-amino alcohols, however their chiral substituted analogues are difficult to access. We established a cascade for the asymmetric azidohydroxylation of styrene derivatives leading to chiral substituted 1,2-azido alcohols via enzymatic asymmetric epoxidation, followed by regioselective azidolysis, affording the azido alcohols with up to two contiguous stereogenic centers. A newly isolated two-component flavoprotein styrene monooxygenase StyA proved to be highly selective for epoxidation with a nicotinamide coenzyme biomimetic as a practical reductant. Coupled with azide as a nucleophile for regioselective ring opening, this chemo-enzymatic cascade produced highly enantioenriched aromatic α-azido alcohols with up to >99% conversion. A bi-enzymatic counterpart with halohydrin dehalogenase-catalyzed azidolysis afforded the alternative β-azido alcohol isomers with up to 94% diastereomeric excess. We anticipate our biocatalytic cascade to be a starting point for more practical production of these chiral compounds with two-component flavoprotein monooxygenases.

Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH

Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E?=?1–16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-β-azido alcohols and (R)-α-azido alcohols (ee???99%) were obtained.

AMIDE DERIVATIVES AS LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS

The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, formula (I) wherein R1. X, m. R2, Y, R3, Z, n, R4. A and B are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS AND THE USES THEREOF

The invention relates to pyridinyl nicotinic acetylcholine receptor ligands, compositions comprising an effective amount of a pyridinyl nicotinic acetylcholine receptor ligand and methods to treat or prevent a condition, such as depression and nicotine dependence, comprising administering to an animal in need thereof an effective amount of a pyridinyl nicotinic acetylcholine receptor ligand.

Efficient biocatalysis for the production of enantiopure (S)-epoxides using a styrene monooxygenase (SMO) and Leifsonia alcohol dehydrogenase (LSADH) system

Herein we report the production of enantiopure epoxides through biocatalysis using recombinant Escherichia coli cells expressing Rhodococcus sp. ST-10 styrene monooxygenase (SMO) and Leifsonia sp. S749 alcohol dehydrogenase (LSADH) genes are described. Rhodococcus sp. ST-10 SMO catalyzed the epoxidation of various alkenes, including styrene derivatives, vinyl pyridines, and linear alkenes, to give (S)-epoxides. NADH was regenerated by the reduction of NAD + by LSADH with 2-propanol. The E. coli biocatalyst was used in an aqueous/organic biphasic reaction system and the reaction conditions were optimized. Under the optimized conditions, 170 mM of (S)-styrene oxide was obtained from styrene in the organic phase with excellent enantiomeric excess (99.8%). This biocatalytic process was used to synthesize various (S)-epoxides.

Enantioselective ring-opening reaction of epoxides with MeOH catalyzed by homochiral metal-organic framework

Two new copper metal-organic frameworks containing 2,2′-dihydroxy-1, 1′-binaphthalene-5,5′-dicarboxylic acid (5,5′-H 2BDA) and 2,2′-dihydroxy-1,1′-binaphthalene-4,4′- dicarboxylic acid (4,4′-H2BDA) have been prepared. X-ray structure determination of [Cu2(5,5′-BDA)2(H 2O)2]·MeOH·2H2O (MOF-1) and [Cu2(4,4′-BDA)2(H2O)2] ·4H2O (MOF-2) revealed similar 2D sheet structures, containing square-grid coordination networks, but differences in the stacking motif. The desolvated MOF-1 and -2 were used as Lewis acid catalysts in the asymmetric ring-opening reaction of epoxides with MeOH.

Synthesis of (R)-selegiline via hydrolytic kinetic resolution

A short and enantioselective formal synthesis of (R)-selegiline has been achieved using Jacobsen's hydrolytic kinetic resolution (HKR) of phenyl propylene oxide.

Styrene monooxygenase from Pseudomonas sp. LQ26 catalyzes the asymmetric epoxidation of both conjugated and unconjugated alkenes

A novel styrene monooxygenase (SMO) was isolated from Pseudomonas sp. LQ26, a styrene degrader from activated sludge. Sequence alignment demonstrated that it was the most distant member of all SMOs originating from the genus of Pseudomonas. The substrate spectrum of this enzyme extended beyond typical SMO substrates to 1-allylbenzene analogues, previously reported as non-substrates for the SMO from Pseudomonas fluorescens ST. The results demonstrate for the first time the asymmetric epoxidation of both conjugated and unconjugated alkenes catalyzed by SMO and suggest that a much broader substrate spectrum is expected for SMOs.

Synthesis of azide-alkyne fragments for "Click" chemical applications. Part 2. Formation of oligomers from orthogonally protected chiral trialkylsilylhomopropargyl azides and homopropargyl alcohols

(Chemical Equation Presented) A small library of chiral, β3-substituted homopropargyl alcohols and chiral β3-substituted trimethylsilylhomopropargyl azides were generated starting from natural L-amino acids. The free alkynes and azides were then coupled, using a Huisgen 1,3-dipolar cycloaddition, to provide chiral oligomeric 1,4-disubstituted-1,2,3-triazoles as potential peptidomimetic compounds. The work is an extension to the previous synthesis of racemic, orthogonally protected 1,4-disubstituted-1,2,3-triazoles from the corresponding α-substituted propargyl alcohols and α-substituted trialkylsilylpropargyl azides.

NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS AND THE USES THEREOF

The invention relates to pyridinyl nicotinic acetylcholine receptor ligands, compositions comprising an effective amount of a pyridinyl nicotinic acetylcholine receptor ligand and methods to treat or prevent a condition, such as depression and nicotine dependence, comprising administering to an animal in need thereof an effective amount of a pyridinyl nicotinic acetylcholine receptor ligand.