157240-36-3

Basic information

• Product Name: (2R,3S)-3-phenylisoserine methyl ester
• Synonyms: (2R,3S)-3-phenylisoserine methyl ester
• CAS NO: 157240-36-3
• Molecular Weight: 195.218
• Mol File: 157240-36-3.mol
• Article Data: 20

Chemical Properties

• Melting Point: 103-106 °C
• Boiling Point: 343.0±42.0 °C(Predicted)
• Density: 1.212±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (2R,3S)-3-phenylisoserine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-3-phenylisoserine methyl ester(157240-36-3)
• EPA Substance Registry System: (2R,3S)-3-phenylisoserine methyl ester(157240-36-3)

Safety Data

• Hazardous Substances Data: 157240-36-3(Hazardous Substances Data)

Usage

General Description

(2R,3S)-3-phenylisoserine methyl ester is a chemical compound with a molecular formula of C12H17NO3. It is an ester derivative of the amino acid phenylisoserine, and it consists of a phenyl group, an isoserine residue, and a methyl ester group. (2R,3S)-3-phenylisoserine methyl ester is used in the field of organic chemistry and drug development as a building block for the synthesis of various pharmaceuticals and biologically active compounds. Its stereochemistry, with the (2R,3S) configuration, is important for its biological activity and interactions with other molecules. It is often synthesized through organic reactions to produce enantiomerically pure samples for research and development purposes.

Upstream product

• 67-56-1 methanol 
• 132201-32-2 (2R,3S)-3-phenylisoserine hydrochloride 
• 157722-41-3 methyl 3-amino-2-keto-3-phenylpropionate 
• 146848-87-5 (+)-isobutyl (2S,3R)-3-phenylglycidate 
• 103-26-4 Methyl cinnamate 
• 19190-80-8 methyl trans-3-phenylglycidate 
• 158810-74-3 (-)-(2R,3S)-methyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate 
• 69350-13-6 N-benzylidene-(S)-α-methylbenzylamine 
• 5321-31-3 phenylglycidylchloride hydrochloride 
• 157722-40-2 (S)-3-Amino-2-oxo-3-phenyl-propionitrile 
• 2935-35-5 (S)-2-phenylglycine 
• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 7780-06-5 isopropyl cinnamate 
• 145987-13-9 methyl (2S,3R)-2-acetoxy-3-bromo-3-phenylpropionate 

Downstream Products

• 335317-39-0 (2S,4S,5R)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-allyl ester 5-methyl ester 
• 335317-25-4 (2S,4S,5R)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-allyl ester 
• 615556-29-1 N-(2-nitrobenzenesulfenyl)-3-phenylisoserine methyl ester 
• 1428799-84-1 methyl-(2R,3S)-2-hydroxy-3-phenyl-3-{[(5-phenyl-1,3,4-oxadiazol-2-yl)-carbonyl]amino}propanoate 
• 153652-71-2 (4S,5R)-2,2-Dimethyl-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester 
• 143615-03-6 (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid 
• 274681-92-4 methyl (2S,3S)-2-azido-3-(tert-butoxycarbonylamino)-3-phenylpropionate 
• 274681-94-6 methyl (2S,3S)-2-amino-3-[(tert-butoxycarbonyl)amino]-3-phenylpropanoate 
• 202390-84-9 Methyl (4S,5R)-3-benzoyl-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylate 
• 153652-70-1 (4S,5R)-3-Benzoyl-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid 
• 196404-55-4 acide (4S,5R)-N-(tert-butoxycarbonyl)-2-(4-O-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylique 
• 114915-20-7 Docetaxel 
• 670254-71-4 (2*,4S,5R)-methyl N-tert-butoxycarbonyl-2-(4'-methoxy)phenyl-4-phenyl-1,3-oxazolidine-5-methionate 
• 133524-69-3 (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl)oxy)-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate 

Relevant articles and documents

Design, synthesis of novel C-3′-N-sulfonyl modified taxane analogues from 1-deoxybaccatin VI and their impact on anti-HCC activity

A new series of C-3′-N-sulfonyl paclitaxel analogs were designed and synthesized from 1-deoxybaccatin VI and their structures were confirmed by 1H NMR, 13C NMR and high resolution MS. The synthesized compounds were evaluated for their in vitro anti-Hepatocellular carcinoma (HCC) activity against human hepatoma (HepG2) cell line. Bioassay results showed that compounds 17c, 17d and 17f exhibited more potent inhibitory activity against HepG2 cell line in comparison with paclitaxel. It is suggested that paclitaxel analogs containing the C-3′-N-sulfonyl could be considered as a precursor structure for further synthesis of more potent analogues.

C-13 and C-7 site structure modified paclitaxel compound and preparing method thereof

The invention relates to a C-13 and C-7 site structure modified paclitaxel compound and a preparing method thereof. A structural formula of the compound is shown in the description, wherein R1 is n-propyl carbonyl, n-amyl carbonyl, 2-thiophene carbonyl, 5

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.