79898-17-2

Basic information

• Product Name: (2S,3R)-3-Phenylglycidic Acid
• Synonyms: (2S,3R)-3-Phenylglycidic Acid
• CAS NO: 79898-17-2
• Molecular Formula: C₉H₈O₃
• Molecular Weight: 164.15802
• Mol File: 79898-17-2.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -86°C Freezer, Under inert atmosphere
• Solubility: Dichloromethane, Ethanol, Ether, Methanol
• CAS DataBase Reference: (2S,3R)-3-Phenylglycidic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-3-Phenylglycidic Acid(79898-17-2)
• EPA Substance Registry System: (2S,3R)-3-Phenylglycidic Acid(79898-17-2)

Safety Data

• Hazardous Substances Data: 79898-17-2(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

(2S,3R)-3-Phenylglycidic Acid (cas# 79898-17-2) is a compound useful in organic synthesis.

Upstream product

• 267003-16-7 (2R,3R)-3-(3-phenyloxiran-2-yl)furan 
• 267003-15-6 trans-(2S,3R)-2-furyl-3-phenyl oxirane 
• 140-10-3 (E)-3-phenylacrylic acid 
• 27992-27-4 sodium 2-benzylidene-1-tosylhydrazin-1-ide 
• 100-52-7 benzaldehyde 
• 2272-55-1 ethyl trans-3-phenyl-1-oxirane-2-carboxylate 
• 19190-80-8 methyl trans-3-phenylglycidate 
• 103-26-4 Methyl cinnamate 
• 146848-87-5 (+)-isobutyl (2S,3R)-3-phenylglycidate 
• 98819-68-2 3-phenyl-(2R,3R)-oxiran-2-ylmethanol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 1566-68-3 (2RS,3SR)-2,3-epoxy-3-phenyl-propionic acid 
• 79898-18-3 (R)-α-methylbenzylammonium (2S,3R)-2,3-epoxy-3-phenylpropionate 

Downstream Products

• 98819-68-2 3-phenyl-(2R,3R)-oxiran-2-ylmethanol 
• 98769-72-3 (-)-(2S,3S)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide 
• 98819-73-9 (+)-(2S,3S)-1-amino-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropane 
• 98819-70-6 (+)-(2R,3S)-3-(2-ethoxyphenoxy)-1,2-dihydro-3-phenylpropane 
• 93886-32-9 (-)-(2S,3S)-6-<α-(2-ethoxyphenoxy)benzyl>morpholin-3-one 
• 71620-89-8 (S,S)-reboxetine 
• 98819-71-7 (+)-(2R,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-1-(4-nitrobenzoyloxy)-3-phenylpropane 
• 98769-71-2 (+)-(2R,3S)-3-(2-ethoxyphenoxy)-2-mesyloxy-1-(4-nitrobenzoyloxy)-3-phenylpropane 
• 122-78-1 phenylacetaldehyde 
• 1452586-11-6 13-O-((2S,3R)-3-phenylglycidoyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin 
• 174729-12-5 13-O-((2R,3R)-3-phenylglycidoyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin 
• 32946-42-2 (2S,3S)-2-amino-3-hydroxy-3-phenylpropanoic acid 
• 6254-48-4 (2S,3R)-3-phenylserine 
• 114376-13-5 (3S,4R,5R)-clausenamidone 

Relevant articles and documents

Efficient synthesis of (-)-clausenamide

A new method for the synthesis of (-)-clausenamide was reported. (-)-clausenamide was obtained from the inexpensive material of trans-cinnamic acid within five steps with overall yields of 8.9% and ee 99.5%. Compared with the multi-step asymmetric synthes

Intermolecular Amine Transfer to Enantioenriched trans-3Phenylglycidates by an α/β-Aminomutase to Access Both anti-Phenylserine Isomers

β-Hydroxy-α-amino acids are noncanonical amino acids with two stereocenters and with useful applications in the pharmaceutical and agrochemical sectors. Here, a 5-methylidene-3,5-dihydro-4H-imidazol-4-one-dependent aminomutase from Taxus canadensis (TcPAM) was repurposed to transfer the amino group irreversibly from (2S)-styryl-α-alanine to exogenously supplied trans-3-phenylglycidate enantiomers, producing anti-phenylserines stereoselectively. TcPAM catalysis inverted the intrinsic regioselective chemistry from amination at Cβ to Cα of enantioenriched trans-3-phenylglycidates to make phenylserine predominantly (97%)phenylisoserine (～3% relative abundance). Gas chromatography?mass spectrometry analysis of the chiral auxiliary derivatives of the biocatalyzed products confirmed that the amine transfer was stereoselective for each glycidate enantiomer. TcPAM converted (2S,3R)-3-phenylglycidate to (2S)-anti-phenylserine predominantly (89%) and (2R,3S)-3-phenylglycidate to (2R)-anti-phenylserine (88%)their antipodes, with inversion of the configuration at Cα in each case. Both glycidate enantiomers formed a small amount (～10%) of syn-phenylserine by retaining the configuration at Cα. The minor syn-isomer likely came from a β-hydroxy oxiranone intermediate formed by intramolecular ring opening of the oxirane ring by the carboxylate before amine transfer. TcPAM had a slight preference toward (2S,3R)-3-phenylglycidate, which was turned(kcat = 0.3 min?1) 1.5 times faster than the (2R,3S)-glycidate (kcat = 0.2 min?1). The catalytic efficiencies (kcatapp/KMapp ≈ 20 M?1s?1) of TcPAM for the antipodes were similar. The kinetic data supported a two-substrate ping-pong mechanism for the amination of the phenylglycidates, with competitive inhibition at higher glycidate substrate concentrations.

Regio- and stereoselective methods for the conversion of (2S,3R)-β-phenylglycidic acid esters to taxoids and other enantiopure (2R,3S)-phenylisoserine esters

A novel efficient method was proposed for the synthesis of enantiopure precursors of taxane-containing cytostatics, i.e., methyl esters of (2R,3S)- and (2S,3R)-N-benzoylphenylisoserine and similar taxoid esters. The method is based on the regio- and stereoselective hydrobromolysis of the corresponding trans-β-phenyl glycidate enatiomers, consecutive reactions of O-acylcarbamoylation of the obtained 3-bromohydrins, intramolecular cyclization to 4-phenyloxazolidin-2-one-5-carboxylic acid derivatives, and oxazolidinone ring opening.