43210-73-7

Basic information

• Product Name: (R)-2-(2-NAPHTHYL)GLYCOLIC ACID
• Synonyms: (R)-2-(2-NAPHTHYL)GLYCOLIC ACID
• CAS NO: 43210-73-7
• Molecular Formula: C₁₂H₁₀O₃
• Molecular Weight: 202.21
• Mol File: 43210-73-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-2-(2-NAPHTHYL)GLYCOLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(2-NAPHTHYL)GLYCOLIC ACID(43210-73-7)
• EPA Substance Registry System: (R)-2-(2-NAPHTHYL)GLYCOLIC ACID(43210-73-7)

Safety Data

• Hazardous Substances Data: 43210-73-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-2-(2-NAPHTHYL)GLYCOLIC ACID is used as a chiral precursor for the synthesis of various drugs, particularly those with anti-inflammatory and anti-cancer properties. Its chiral nature allows for the production of enantiomerically pure compounds, which is essential for the development of effective and safe medications.
Used in Medicinal Chemistry:
(R)-2-(2-NAPHTHYL)GLYCOLIC ACID is used as a key intermediate in the development of new pharmaceuticals, particularly those targeting inflammation and cancer. Its unique structure and properties make it a valuable building block for the design and synthesis of novel therapeutic agents.
Used in Organic Synthesis:
(R)-2-(2-NAPHTHYL)GLYCOLIC ACID is used as a versatile building block in organic synthesis, particularly in asymmetric synthesis processes. Its chiral nature allows for the selective formation of specific enantiomers, which is crucial for the development of biologically active compounds with desired properties.

Upstream product

• 20861-93-2 Isopropylaminomethyl-2-naphthyl-keton-hydrobromid 
• 62-76-0 sodium oxalate 
• 66-99-9 β-naphthaldehyde 
• 20862-03-7 2-naphthyl cyanohydrin 
• 93-08-3 methyl 2-naphthyl ketone 
• 91395-22-1 2,2-dichloro-1-(naphthalen-2-yl)ethan-1-one 
• 475582-21-9 α-methoxy-2-naphthylacetamide 
• 126644-23-3 α-acetoxy-2-naphthylacetonitrile 
• 118736-08-6 α-methoxy-2-naphthylacetonitrile 
• 126567-33-7 (R)-(-)-1-cyano-1-(2-naphthyl)methyl acetate 
• 77196-31-7 2-(dimethoxymethyl)naphthalene 
• 475582-26-4 (R)-α-hydroxy-2-naphthylacetamide 
• 14289-44-2 (RS)-2-naphthylglycolic acid 
• 22115-06-6 2-naphthylglyoxal 

Downstream Products

• 156942-67-5 (R)-α-methoxynaphthalen-2-ylacetic acid 

Relevant articles and documents

Asymmetric reduction of arylglyoxylic acids via host-guest complex formation with optically active paracyclophanes

Reduction of 1-naphthylglyoxylic acid (2c) by inclusion complex formation with optically active paracyclophane (1a) followed by treatment with sodium borohydride in acidic water gave, after esterification with diazomethane, (R)-1-naphthylglycolic acid methyl ester (4c) in 9.7% ee. A working hypothesis is proposed to describe the mechanism of this reaction.

Oxalyl-CoA Decarboxylase Enables Nucleophilic One-Carbon Extension of Aldehydes to Chiral α-Hydroxy Acids

The synthesis of complex molecules from simple, renewable carbon units is the goal of a sustainable economy. Here we explored the biocatalytic potential of the thiamine-diphosphate-dependent (ThDP) oxalyl-CoA decarboxylase (OXC)/2-hydroxyacyl-CoA lyase (HACL) superfamily that naturally catalyzes the shortening of acyl-CoA thioester substrates through the release of the C1-unit formyl-CoA. We show that the OXC/HACL superfamily contains promiscuous members that can be reversed to perform nucleophilic C1-extensions of various aldehydes to yield the corresponding 2-hydroxyacyl-CoA thioesters. We improved the catalytic properties of Methylorubrum extorquens OXC by rational enzyme engineering and combined it with two newly described enzymes—a specific oxalyl-CoA synthetase and a 2-hydroxyacyl-CoA thioesterase. This enzymatic cascade enabled continuous conversion of oxalate and aromatic aldehydes into valuable (S)-α-hydroxy acids with enantiomeric excess up to 99 %.

Hydrogen-bonding sheets in crystals for chirality recognition: synthesis and application of (2S,3S)-2,3-dihydroxy- and (2S,3S)-2,3-dibenzyloxy-1,4-bis(hydroxyamino)butanes

Two enantiopure bis(hydroxyamino) compounds were successfully prepared from dialkyl tartrate by a chiral-pool method and applied as basic resolving agents in the enantioseparation of 2-arylpropanoic acids and arylglycolic acids. (2S,3S)-2,3-Dihydroxy-1,4-bis(hydroxyamino)butane (2S,3S)-1a could moderately recognize the chirality of the 2-arylpropanoic acids, while (2S,3S)-2,3-dibenzyloxy-1,4-bis(hydroxyamino)butane (2S,3S)-1b could not due to the low crystallinity of both the corresponding diastereomeric salts. On the other hand, (2S,3S)-1b showed a similar chirality-recognition ability for the arylglycolic acids. The ability of (2S,3S)-1b was different from those generally observed for widely used primary amine-type resolving agents with regard to the relationship between the resolution efficiency and the similarity in the relative molecular length of a resolving agent and a target racemate. The X-ray crystallographic analyses of the less-soluble diastereomeric salts revealed that in the salts (2S,3S)-1a formed a supramolecular sheet, of which the distance was variable to make the resultant dissymmetric space fit to the shape of the target acids, and that (2S,3S)-1b was constructed from a robust supramolecular sheet, consisting of hydrogen-bonding 21 columns, with the participation of the hydroxy group of the arylglycolic acids. These X-ray crystallographic analyses also suggested that for the formation of a supramolecular sheet, the coexistence of two hydroxyamino groups is essential.

Process for preparing optically active amines and optically active carboxylic acids, and intermediates for preparation

Disclosed is a process for preparing an optically active 1-aryl- or 2-aryl-alkylamines of formulas Ia, Ib and Ic with high optical purity and high yield. The process uses an optically active 1- or 2-naphthylglycolic acid of the general formula II as a resolving agent. Also disclosed is a process for praparing an optically active 1- or 2-naphthylglycolic acid of formula II using an optically active 1-aryl- or 2-aryl-alkylamines of formulas Ia, Ib and Ic as the resolving agents

Chemo-enzymatic synthesis of enantiomerically pure (R)-2-naphthylmethoxyacetic acid

Enantiomerically pure (R)-2-naphthylmethoxyacetic acid (2-NMA) was synthesized from 2-naphthaldehyde via an integrated chemo-enzymatic procedure. The one-pot, successive use of SnBr2-TMSCN and AcBr worked effectively to give a racemic cyanohydrin acetate. Lipase from Burkholderia cepacia then mediated the highly enantioselective hydrolysis of the (S)-enantiomer of the racemate, leaving the (R)-acetate with an e.e. of >99.9%. The resulting product of this enzyme-catalyzed hydrolysis, an (S)-cyanohydrin, spontaneously decomposed into naphthaldehyde, the starting material of this synthetic route, which could be recycled. The hydration of nitrile to amide as well as the hydrolysis of the acetate was performed with a microorganism, Rhodococcus rhodochrous, under very mild conditions without any loss of the enantiomeric purity. The amide group was hydrolyzed with nitrosylsulfuric acid, and the product was isolated as an α-hydroxy ester. The α-hydroxyl group was methylated with diazomethane-silica gel and the final task, hydrolysis of the ester, was accomplished under conditions as mild as neutral pH with an esterase from Krebsiella oxytoca to give enantiomerically pure 2-NMA.

An enzyme library approach to biocatalysis: Development of nitrilases for enantioselective production of carboxylic acid derivatives

The discovery, from Nature, of a large and diverse set of nitrilases is reported. The utility of this nitrilase library for identifying enzymes that catalyze efficient production of valuable hydroxy carboxylic acid derivatives is demonstrated. Unprecedented enantioselectivity and substrate scope are highlighted for three newly discovered and distinct nitrilases. For example, a wide array of (R)-mandelic acid derivatives and analogues were produced with high rates, yields, and enantiomeric excesses (95-99% ee). We also have found nitrilases that provide direct access to (S)-phenyllactic acid and other aryllactic acid derivatives, again with high yields and enantioselectivities. Finally, different nitrilases have been discovered that catalyze enantiotopic hydrolysis of 3-hydroxyglutaronitrile to afford either enantiomer of 4-cyano-3-hydroxybutyric acid with high enantiomeric excesses (>95% ee). The first enzymes are reported that effect this transformation to furnish the (R)-4-cyano-3-hydroxybutyric acid which is a precursor to the blockbuster drug Lipitor. Copyright

A high-performance, tailor-made resolving agent: Remarkable enhancement of resolution ability by introducing a naphthyl group into the fundamental skeleton1

A novel resolving agent, 2-naphthylglycolic acid (2-NGA), was designed for p-substituted 1-arylethylamines on the basis of the consideration that a rigid and large naphthyl group would be favorable for the close packing of supramolecular hydrogen-bond sheets formed between the carboxy groups of 2-NGA and the amino groups of p-substituted 1-arylethylamines. Racemic 2-NGA was readily available from commercially available raw materials, and both enantiopure forms could be obtained by simple diastereomeric resolution with enantiopure 1-phenyl-ethylamine. Thus-prepared enantiopure 2-NGA was found to have an excellent resolution ability not only for p-substituted 1-arylethylamines, but also for a wide variety of chiral primary amines. X-Ray crystallographic analyses of the less- and more-soluble diastereomeric salts revealed that this excellent resolution ability of 2-NGA arose from the formation of a supramolecular hydrogen-bond sheet with the primary amine, as we had expected, and also from the possible achievement of an infinite chain of CH... π interaction between its naphthyl group and the aromatic group of the amine, which was formed in the hydrophobic region of the supramolecular hydrogen-bond sheet.

(2-naphthyl)glycolic acid: A tailored resolving agent for p-substituted 1-arylethylamines

A tailored resolving agent for p-substituted l-arylethylamines, which was designed on the basis of a criterion derived from our crystal-structure study, namely that the racemate and the resolving agent should have similar molecular lengths, is described. The designed enantiopure (2- naphthyl)glycolie acid (2-NGA) showed excellent resolving ability for a wide variety of p-substituted l-arylethylamines.