85879-96-5

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-2-acetoxy-2-phenylacetic acid ethyl ester is used as an intermediate in the synthesis of pharmaceuticals for its ability to react with other compounds to form new molecules with potential medicinal properties.
Used in Organic Chemistry:
In the field of organic chemistry, (S)-2-acetoxy-2-phenylacetic acid ethyl ester is used as a reagent or a building block for the creation of more complex organic compounds due to its versatile chemical structure.
Used in Research and Development:
(S)-2-acetoxy-2-phenylacetic acid ethyl ester is also utilized in research and development for studying its properties and potential applications in various scientific fields, including material science and chemical engineering.
Used in Fragrance and Flavor Production:
Due to its aromatic properties, (S)-2-acetoxy-2-phenylacetic acid ethyl ester is used as a component in the production of fragrances and flavors, adding unique scents and tastes to various products.
Used in the Chemical Industry:
In the chemical industry, (S)-2-acetoxy-2-phenylacetic acid ethyl ester may be employed as a specialty chemical for specific applications, taking advantage of its unique chemical structure and reactivity.

Upstream product

• 876-27-7 4-chlorophenyl acetate 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 108-24-7 acetic anhydride 
• 13704-09-1 (S)-(-)-ethyl mandelate 
• 74327-04-1 ethyl 2-acetoxy-2-phenylacetate 
• 108-05-4 vinyl acetate 
• 611-71-2 MANDELIC ACID 
• 100-52-7 benzaldehyde 
• 532-28-5 (RS)-mandelonitrile 
• 123-20-6 vinyl n-butyrate 
• 1122-58-3 dmap 
• 29071-09-8 2-acetoxy-2-phenylacetic acid 
• 538-75-0 dicyclohexyl-carbodiimide 
• 7322-88-5 (S)-acetylmandelic acid 

Downstream Products

• 851705-13-0 C₁₂H₁₃NO₆ 
• 851705-12-9 C₁₂H₁₃NO₆ 
• 791074-34-5 (S)-[(4S)-4-tert-butyl-4,5-dihydrooxazol-2-yl](phenyl)methyl acetate 
• 928013-75-6 (S)-[(4S)-4-benzyl-4,5-dihydrooxazol-2-yl](phenyl)methyl acetate 
• 928013-74-5 (S)-[(4S)-4-isobutyl-4,5-dihydrooxazol-2-yl](phenyl)methyl acetate 
• 928013-76-7 (S)-[(4S)-4-isopropyl-4,5-dihydrooxazol-2-yl](phenyl)methyl acetate 
• 928013-73-4 (S)-[(4S)-4-methyl-4,5-dihydrooxazol-2-yl](phenyl)methyl acetate 
• 791074-28-7 (S,S)-O-acetylmandelic acid (1-hydroxymethyl-2,2-dimethyl)propylamide 

Relevant academic research and scientific papers

Synthetically useful variants of industrial lipases from: Burkholderia cepacia and Pseudomonas fluorescens

Industrial enzymes lipase PS (LPS) and lipase AK (LAK), which originate from Burkholderia cepacia and Pseudomonas fluorescens, respectively, are synthetically useful biocatalysts. To strengthen their catalytic performances, we introduced two mutations into hot spots of the active sites (residues 287 and 290). The LPS-L287F/I290A double mutant showed high catalytic activity and enantioselectivity for poor substrates for which the wild-type enzyme showed very low activity. The LAK-V287F/I290A double mutant was also an excellent biocatalyst with expanded substrate scope, which was comparable to the LPS-L287F/I290A double mutant. Thermodynamic parameters were determined to address the origin of the high enantioselectivity of the double mutant. The ΔΔH? term, but not the ΔΔS? term, was predominant, which suggests that the enantioselectivity is driven by a differential energy associated with intermolecular interactions around Phe287 and Ala290. A remarkable solvent effect was observed, giving a bell-shaped profile between the E values and the log&P or ? values of solvents with the highest E value in i-Pr2O. This suggests that an organic solvent with appropriate hydrophobicity and polarity provides the double mutant with some flexibility that is essential for excellent catalytic performance.

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.

Lipase activity of Lecitase Ultra: characterization and applications in enantioselective reactions

The general properties of Lecitase Ultra, a phospholipase manufactured and marketed by Novozymes, Denmark, have been studied after purification by ultrafiltration. The enzyme has a molecular mass of 35 KD, pH-optimum of 8.5, and appears to possess a single active site which exhibits both the lipase and phospholipase activities that increase in the presence of Ca2+ and Mg2+ ions. The enzyme is inhibited by heavy metal ions and surfactants, and does not accept p-nitrophenyl acetate and glycerol triacetate. Substrates, such as glycerol tributyrate and p-nitrophenyl palmitate, esters of N-acetyl-α-amino acids and α-hydroxy acids are readily accepted. Amino acids with aliphatic residues, such as alanine, isoleucine, and methionine, are hydrolyzed with high enantioselectivity for the l-enantiomer (E >100), but amino acids with aromatic residues such as phenylalanine and phenylglycine, and esters of α-hydroxy acids are hydrolyzed with low enantioselectivity (E = 1-5). Immobilization of the enzyme in a gelatin matrix (gelozyme) leads to a marginal improvement in the enantioselectivity for these substrates. However, a dramatic improvement in enantioselectivity is observed for ethyl 2-hydroxy-4-oxo-4-phenylbutyrate (E value increases from 4.5 to 19.5 with S-selectivity). Similarly, glycidate esters, such as ethyl trans-(±)-3-phenyl glycidate and methyl trans-(±)-3-(4-methoxyphenyl) glycidate, are selectively hydrolyzed with a remarkable selectivity towards the (2S,3R)-enantiomer providing unreacted (2R,3S)-glycidate esters (ee >99%, conversion 52-55%) by the immobilized enzyme.

Convenient synthesis of a new class of chiral hydroxymethyl-dihydrooxazole ligands and their application in asymmetric addition of diethylzinc to aromatic aldehydes

A number of chiral hydroxymethyl-substituted dihydrooxazoles were synthesized from D- or L-mandelic acid and amino alcohols. The chiral ligands thus obtained were tested as catalyst in the asymmetric addition of diethylzinc to aromatic aldehydes, and the

BIPIPERIDINYL DERIVATIVES USEFUL AS INHIBITORS OF CHEMOKINE RECEPTORS

In its many embodiments, the present invention provides a novel class of bipiperidinyl compounds as inhibitors of the CCR5 receptors, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with CCR5 using such compounds or pharmaceutical compositions. The invention also relates to the use of a combination of a compound of this invention and one or more antiviral or other agents useful in the treatment of Human Immunodeficiency Virus (HIV). The invention further relates to the use of a compound of this invention, alone or in combination with another agent, in the treatment of solid organ transplant rejection, graft v. host disease, arthritis, rheumatoid arthritis, inflammatory bowel disease, atopic dermatitis, psoriasis, asthma, allergies or multiple sclerosis.

Dynamic kinetic resolution of α-hydroxy acid Esters

Enzymatic resolution in combination with ruthenium-catalyzed racemization of the substrate led to dynamic kinetic resolution of α-hydroxy esters in good yields and excellent ee's. Studies of different parameters showed that the best results were obtained

Selective binding and activation of one aldehyde enantioface by a chiral transition-metal Lewis acid: Synthesis, structure, and reactivity of rhenium aldehyde complexes [(η5-C5H5)Re(NO)(PPh 3)(η2-O=CHR)]+X-

Reaction of dichloromethane complex [(η5-C5H5)Re(NO)(PPh3)(ClCH 2Cl]+X- (2+PF6- or 2+BF4-) and RCH=O (R = (a) CH3, (b) C2H5, (c) n-C3H7, (d) i-C3H7, (e) C6H5, (f) CH2C6H5) gives π-aldehyde complexes (RS,SR)-[(η5-C5H5)Re(NO)(PPh 3)(η2-O=CHR)]+X- ((RS,SR)-3a-f+X-, 98-77%), in which one RCH=O enantioface is bound with high specificity. Crystal structures of (RS,SA)-3b+BF4- and (RS,SR)-3T*PP6- show the RCH=O carbon to be anti to the PPh3 ligand and the RCH=O group to be syn to the NO ligand. Formyl complex (η5-C5H5)Re(NO)(PPh3)(CHO) (5) and (RS,SR)-3a-f+X- react at -80 °C to give [(η5-C5H5)Re(NO)(PPh3)(CO)] +X- and alkoxide complexes (η5-C5H5)Re(NO)(PPh3)(OCH 2R) (6a-f, 95-80%). Reaction of deuterioformyl complex 5-d1 and (RS,SR)-3a-f+X- gives deuterioalkoxide complexes (η5-C5H5)Re(NO)(PPh3)(OCHDR) (6a-f-d1) as 97-92:3-8 mixtures of (RR,SS)/(RS,SR) diastereomers. Analogous reactions starting with optically active 2+X- give optically active aldehyde and alkoxide complexes with retention of configuration at rhenium. The latter react with electrophiles EX (EX = HI, (CH3)3Sil, CH3COI) to give cleavage products EOCH2R and (η5-C5H5)Re(NO)(PPh3)(X), generally with retention at rhenium. When (+)-(RS)-3a-f+BF4- are treated with (+)-(S)-5-d1 and (-)-(R)-5-d1, (+)-6a-f-d1 form as 99-94:1-6 and 91-84:9-16 mixtures of (RR)/(RS) diastereomers, respectively. Hence, enantiomers of the chiral reductant 5-d1 give different stereoselectivities. Reaction of (+)-6a-f-d1 with (-)-(R)-C6H5CH-(OAc)COOH/DCC/4-(dimethylamino)pyridine gives esters C6H5CH(OAc)COOCHDR that are comparable mixtures of (RR)/(RS) diastereomers and carboxylate (+)-(RR)-(η5-C5H5)Re(NO)(PPh 3)(O(C=O)CH(OAc)C6H5) of >99% de.

1H and 2H Nuclear Magnetic Resonance Determination of the Enantiomeric Purity and Absolute Configuration of α-Deuteriated Primary Carboxylic Acids, Alcohols, and Amines

The enentiomeric composition and absolute configuration of α-deuteriated primary carboxylic acids may be accurately determined by 1H and 2H nuclear magnetic resonance analysis of the corresponding esters of (S)-methyl 2-hydroxy-2-phenylethanoate (2).Simil