124718-93-0

Upstream product

• 96-09-3 styrene oxide 
• 51267-50-6 4-phenyl-1,3,2-dioxathiolane 2-oxide 
• 105256-36-8 1-azido-1-phenyl-2-(trimethylsilyloxy)ethane 
• 4648-54-8 trimethylsilylazide 
• 135277-63-3 1-acetoxy-2-azido-2-phenyl ethane 
• 100-42-5 styrene 
• 93-56-1 phenylethane 1,2-diol 
• 33942-00-6 1-acetoxy-2-chloro-2-phenylethane 
• 68-12-2 N,N-dimethyl-formamide 
• 532-27-4 1-chloroacetophenone 
• 4509-09-5 Methyl (+/-)-3,4-epoxybutanoate 

Downstream Products

• 102089-74-7 tert-butyl 2-hydroxy-1-phenylethylcarbamate 
• 135277-63-3 1-acetoxy-2-azido-2-phenyl ethane 
• 86217-38-1 4-phenyl-2-oxazolidinone 
• 20989-17-7 Phenylglycinol 
• 866886-07-9 C₂₂H₂₈N₆O₂ 
• 1050393-63-9 1-[1-(2-hydroxy-1-phenyl-ethyl)-1H-[1,2,3]triazol-4-yl]-1-phenyl-ethanol 
• 1050393-54-8 2-phenyl-2-(4-m-tolyl-[1,2,3]triazol-1-yl)-ethanol 

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.

Preparation of Vicinal Azidohydrins by Reaction of Oxiranes with Triethylaluminium/Hydrogen Azide

A novel, mild, and highly stereoselective transformation of epoxides to azidohydrins by treatment with Et3Al/HN3 in toluene is described.As an example for the versatility of the reaction, a polyfunctional compound, 14,15-epoxy-14,15-dihydromilbemycin D (1), was transformed to 14-azido-14,15-dihydro-15-hydroxymilbemycin D (2) in 61 percent yield.

Regioselective azidolysis of epoxides catalyzed with Ce(IV)

Regioselective conversion of epoxides to 1,2-azidoalcohols was performed efficiently with sodium azide in t-butanol and in the presence of catalytic amounts of Ce(IV) as ceric ammonium nitrate (CAN).

Efficient one-pot click synthesis of β-hydroxy-1,2,3-triazoles catalyzed by copper(i)@phosphorated SiO2via multicomponent reaction in aqueous media

Copper(i)-modified SiO2, in particular Cu(i)@phosphorated SiO2 (CPSi) has been found to effectively catalyze the multi-component synthesis of β-hydroxy-1,2,3-triazoles from a variety of epoxides and alkynes in water. This novel heter

Highly α-position regioselective ring-opening of epoxides catalyzed by halohydrin dehalogenase from: Ilumatobacter coccineus: A biocatalytic approach to 2-azido-2-aryl-1-ols

Halohydrin dehalogenases are usually recognized as strict β-position regioselective enzymes in the nucleophile-mediated ring-opening of epoxides. Here we found the HheG from Ilumatobacter coccineus exhibited excellent α-position regioselectivity in the az

CuO supported 1-methyl-3-(3-(trimethoxysilyl) propyl) imidazolium chloride (MTMSP-Im/Cl) nanoparticles as an efficient simple heterogeneous catalysts for synthesis of β-azido alcohols

In the present study, CuO supported 1-methyl-3-(3-(trimethoxysilyl) propyl) imidazolium chloride (MTMSP-Im/Cl) is synthesized as a novel, efficient and eco-friendly heterogeneous nanocatalyst. This nanocatalyst was applied for selective ring opening of ep

Iron-Catalysed Remote C(sp3)?H Azidation of O-Acyl Oximes and N-Acyloxy Imidates Enabled by 1,5-Hydrogen Atom Transfer of Iminyl and Imidate Radicals: Synthesis of γ-Azido Ketones and β-Azido Alcohols

In the presence of a catalytic amount of iron(III) acetylacetonate [Fe(acac)3], the reaction of structurally diverse ketoxime esters with trimethylsilyl azide (TMSN3) afforded γ-azido ketones in good to excellent yields. This unprecedented distal γ-C(sp3)?H bond azidation reaction went through a sequence of reductive generation of an iminyl radical, 1,5-hydrogen atom transfer (1,5-HAT) and iron-mediated redox azido transfer to the translocated carbon radical. TMSN3 served not only as a nitrogen source to functionalise the unactivated C(sp3)?H bond, but also as a reductant to generate the catalytically active FeII species in situ. Based on the same principle, a novel β-C(sp3)?H functionalisation of alcohols via N-acyloxy imidates was subsequently realised, leading, after hydrolysis of the resulting ester, to β-azido alcohols, which are important building blocks in organic and medicinal chemistry.

Montmorillonite K10 catalyzed highly regioselective azidolysis of epoxides: A short and efficient synthesis of phenylglycine

A series of β‐hydroxyazides were effectively synthesized from the regioselective ring opening of epoxides by sodium azide using montmorillonite K10 as a novel heterogeneous catalyst in aqueous acetonitrile in good to excellent yields. The utility of this method has been demonstrated by achieving a short synthesis of phenylglycine in 33.5% overall yield.

Synthesis and characterization of a novel nanomagnetic phase-transfer catalyst and its application to regioselective synthesis of β-azido and β-nitro alcohols in water

Immobilization of polyethylene glycol-substituted 1-methylimidazolium bromide on the surface of magnetic Fe3O4 nanoparticles through hexane-1,6-diyldicarbamate linker afforded a powerful and reusable heterogeneous phase-transfer cata

Hydrotrope promoted in situ azidonation followed by copper catalyzed regioselective synthesis of β-hydroxytriazoles

Abstract: The rapid method for the synthesis of organic azides was achieved by employing azide acceptors such as halides, epoxides and pseudohalides like diazonium salts and aryl boronic acids in hydrotropic media. In extension, the sequential multicomponent reaction of epoxides, azide and alkynes using copper catalysis has been discussed. The reaction proceeds via the in situ generation of azido-alcohol followed by synthesis of chiral β-hydroxytriazoles. This [3?+?2] cycloaddition reaction of azide and alkyne using copper catalysis serves as a green and efficient protocol in “Click Chemistry”. The nucleophilic addition of azide to epoxide and alkyne-azide cycloaddition is the two simultaneous regioselective click reactions observed in the proposed method. Graphical Abstract: [Figure not available: see fulltext.].