79416-45-8

Usage

Uses

Used in Pharmaceutical Industry:
(+)-Methyl (S)-α-acetoxyphenylacetate is used as an intermediate in the synthesis of various pharmaceuticals for its potential medicinal properties. It plays a crucial role in the development of new drugs and medicines.
Used in Perfume Industry:
(+)-Methyl (S)-α-acetoxyphenylacetate is used as an intermediate in the synthesis of perfumes, contributing to the creation of unique and complex fragrances.
Used in Organic Compounds Synthesis:
(+)-Methyl (S)-α-acetoxyphenylacetate is used as a building block for the synthesis of various organic compounds, showcasing its versatility in organic chemistry.
Used in Natural Products Synthesis:
(+)-Methyl (S)-α-acetoxyphenylacetate is used in the synthesis of various natural products, highlighting its importance in replicating and understanding the structure and properties of naturally occurring compounds.
Used as Anti-Inflammatory Agent:
(+)-Methyl (S)-α-acetoxyphenylacetate is studied for its potential as an anti-inflammatory agent, indicating its possible use in the development of treatments for inflammatory conditions.
Used as Antioxidant Agent:
(+)-Methyl (S)-α-acetoxyphenylacetate is also studied for its potential as an antioxidant agent, suggesting its possible application in the development of therapies to combat oxidative stress-related diseases.

Upstream product

• 7322-88-5 (S)-acetylmandelic acid 
• 108-05-4 vinyl acetate 
• 4358-87-6 (RS)-methyl mandelate 
• 21210-43-5 (S)-Methyl mandelate 
• 108-24-7 acetic anhydride 
• 802294-64-0 propionic acid 
• 64-19-7 acetic acid 
• 86561-27-5 methyl O-acetylmandalate 
• 876-27-7 4-chlorophenyl acetate 
• 611-71-2 MANDELIC ACID 
• 100-52-7 benzaldehyde 
• 51019-43-3 (R)-(-)-O-acetylmandelic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 1071508-40-1 (α-(acetyloxy)benzyl)tributylstannane 

Downstream Products

• 21210-43-5 (S)-Methyl mandelate 

Relevant academic research and scientific papers

Chemoenzymatic Preparation of Enantiomerically Enriched (R)-(–)-Mandelic Acid Derivatives: Application in the Synthesis of the Active Agent Pemoline

The enantioselective resolution of several racemic derivatives of mandelic acid methyl ester catalyzed by lipases from Pseudomonas fluorescens (Amano AK) or Burkholderia cepacia (Amano PS-C II and Amano PS-IM) has been achieved. A gram-scale lipase-mediated kinetic resolution approach has been developed that allows the facile synthesis of the corresponding methyl (R)-(–)-mandelates with excellent enantiomeric excesses (up to >99 % ee) and reaction enantioselectivity (E values up to >200). The dopaminergic agent pemoline, used in the treatment of attention-deficit hyperactivity disorder (ADHD) and narcolepsy, was synthesized with 98 % ee in a straightforward route by condensing the prepared methyl (R)-(–)-mandelate with guanidine hydrochloride under basic conditions. The desired (R)-(+)-pemoline in optically pure form (>99 % ee) was obtained after two recrystallizations from ethanol. However, it was confirmed by chiral HPLC that optically active pemoline undergoes racemization in methanol solution.

Remarkably improved stability and enhanced activity of a: Burkholderia cepacia lipase by coating with a triazolium alkyl-PEG sulfate ionic liquid

Three types of triazolium cetyl-PEG10 sulfate ionic liquid were synthesized and their activation of Burkholderia cepacia lipase was investigated; both the reaction rate and enantioselectivity depended on the cationic part of the coating ILs and 1-butyl-3-methyl-1,2,3-triazolium cetyl-PEG10 sulfate (Tz1)-coated lipase PS, which is especially suitable for the transesterification of 1-(pyridin-2-yl)ethanol, 1-(pyridin-3-yl)ethanol, and 1-(pyridin-4-yl)ethanol, among 12 types of tested secondary alcohol. The most important result was obtained when these enzymes were stored in an IL ([N221MEM][Tf2N]) solvent: Tz1-PS showed an amazing stability and it exhibited an excellent activity after 2 years when the enzyme was stored in [N221MEM][Tf2N].

Batch and Continuous-Flow One-Pot Processes using Amine Diazotization to Produce Silylated Diazo Reagents

A novel synthesis of trimethylsilyldiazomethane (TMSCHN2) by diazotization of trimethylsilylmethylamine (TMSCH2NH2) is reported using batch and continuous flow synthesis. The latter affords a daily production of 275 g (2.4 mol) of TMSCHN2. Other silylated methylamines were also successfully reacted under the developed reaction conditions to furnish various silicon-bearing diazomethane reagents. The applicability of the process is highlighted by disclosure of batch and continuous flow one-pot esterification and 1,3-dipolar cycloaddition processes. Furthermore, the high-yielding esterification of carboxylic acids with silylated and substituted methylamines in continuous flow is disclosed. Finally, work-up and purification procedures are reported for the preparation of a 2-MeTHF solution of TMSCHN2, which can be used in rhodium-catalyzed methylenation and homologation reactions.

The assignment of the configuration for α-hydroxy acid esters using a CEC strategy

A simple and efficient 1H NMR method for determining the absolute configuration of chiral α-hydroxy acid esters using a competing enantioselective conversion (CEC) strategy was developed. The α-hydroxy acid esters were acylated in the presence

Kinetic resolution of mandelate esters via stereoselective acylation catalyzed by lipase PS-30

By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic mandelate esters has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 197.5. Substituent effect is briefly discussed.

Synthesis of arylglycine and mandelic acid derivatives through carboxylations of α-amido and α-acetoxy stannanes with carbon dioxide

Incorporation reactions of carbon dioxide (CO2) with N-Boc-α-amido and α-acetoxy stannanes were developed using CsF as a mild tin activator. Monoprotected α-amido stannanes could be used, and the corresponding arylglycine derivatives were obtained in moderate-to-high yields under 1 MPa (10 atm) of CO2 pressure. α-Acetoxy stannanes also underwent carboxylation to afford mandelic acid derivatives in excellent yields under ambient CO2 pressure. Both transformations enabled the synthesis of α-tertiary and α-quaternary carboxylic acid derivatives. In addition, the chirality of (S)-N-tert-butylsulfonyl-α- amido stannanes was transferred with up to 90% inversion of configuration at 100 °C.

Increased enantioselectivity and remarkable acceleration of lipase-catalyzed transesterification by using an imidazolium PEG-Alkyl sulfate ionic liquid

Several types of imidazolium salt ionic liquids were prepared derived from poly(oxyethylene)alkyl sulfate and used as an additive or coating material for lipase-catalyzed transesterification in an organic solvent. A remarkably increased enantioselectivity was obtained when the salt was added at 3-10 mol % versus substrate in the Burkholderia cepacia lipase (lipase PS-C)-catalyzed transesterification of 1-phe nylethanol by using vinyl acetate in diisopropyl ether or a hexane solvent system. In particular, a remarkable acceleration was accomplished by the ionic liquid coating with lipase PS in an iPr2O solvent system while maintaining excellent enantioselectivity; it reached approximately 500- to 1000-fold acceleration for some substrates with excellent enantioselectivity. A similar acceleration was also observed for IL1-coated Candida rugosa lipase. MALDITOF mass spectrometry experiments of the ionic-liquid-coated lipase PS suggest that ionic liquid binds with lipase protein.

Kinetic resolution of α-acetoxy N-acyl oxazolidinethiones by a chiral O-nucleophilic acyl transfer catalyst

The kinetic resolution of α-acetoxy N-acyl oxazolidinethiones using the chiral, nonracemic O-nucleophilic acyl transfer catalyst 8 is described. The reaction proceeds on a variety of substrates in excellent yields, with s-factors ranging from 17 to 31. Copyright

Lewis acid catalyzed acylation reactions: Scope and limitations

Acylation of alcohols, thiols, and sugars were studied with a variety of Lewis acids, and it was found that Cu- and Sn(OTf)2 are very efficient in catalyzing the reaction under mild conditions. Among these two catalysts, Cu(OTf)2 was preferred because of its lower cost and relatively higher yield of the acylated product. The reaction was studied in several solvents, but CH2Cl2 was preferred. It was also observed that the present method is suitable for acylation of tertiary alcohols. Sugars were also acylated without any epimerization at the anomeric center. It is further shown here that this method is also suitable for selective acylation of primary or secondary alcohols over tertiary ones.

Pseudomonas sp. lipase immobilized in polymers versus the use of free enzyme in the resolution of (R,S)-methyl mandelate

In the present report, we describe the preparative-scale resolution of (R,S)-methyl mandelate by acylation with vinyl acetate catalyzed by free Pseudomonas sp. lipase or immobilized in poly(ethylene) oxide (PEO) and agar gel, in organic media. Under exper