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

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

Uses

Used in Organic Chemistry:
(2R,3S)-3-phenylisoserine methyl ester is used as a building block in the synthesis of various pharmaceuticals and biologically active compounds due to its unique structure and functional groups.
Used in Drug Development:
(2R,3S)-3-phenylisoserine methyl ester is used as a key intermediate in the development of new drugs, particularly in the pharmaceutical industry. Its specific stereochemistry allows for targeted interactions with biological targets, potentially leading to more effective and selective medications.
Used in Research and Development:
(2R,3S)-3-phenylisoserine methyl ester is used as a research compound to study its properties and potential applications in various fields. Enantiomerically pure samples are often synthesized for research purposes to ensure accurate results and understanding of its biological activity.

Upstream product

• 147058-27-3 methyl (2R,3S)-2-hydroxy-3-phenyl-3-<(S)-1-methylbenzylamino>propanoate 
• 157722-41-3 methyl 3-amino-2-keto-3-phenylpropionate 
• 67-56-1 methanol 
• 136561-53-0 (2R,3S)-2-hydroxy-3-amino-3-phenylpropionic acid 
• 99458-15-8 Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate 
• 132201-32-2 (2R,3S)-3-phenylisoserine hydrochloride 
• 878395-97-2 (S_S,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine methyl ester 
• 186249-74-1 (S,E)-N-benzylidene-tert-butylsulfinamide 
• 140-10-3 (E)-3-phenylacrylic acid 
• 60512-85-8 (E)-isopropyl cinnamate 
• 195624-97-6 (2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester 
• 122743-18-4 methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate 
• 103-26-4 Methyl cinnamate 
• 145987-13-9 methyl (2S,3R)-2-acetoxy-3-bromo-3-phenylpropionate 

Downstream Products

• 157722-42-4 (2R,3S)-3-Amino-3-phenyl-2-trimethylsilanyloxy-propionic acid methyl ester 
• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 176298-46-7 2-hydroxy-3-(4-methyl benzenesulfonylamino)-3-phenyl-propionic acid methyl ester 
• 335317-38-9 (2R,3S)-3-Allyloxycarbonylamino-2-hydroxy-3-phenyl-propionic acid methyl ester 
• 412317-95-4 (2R,3S)-N-(4-azidobenzyloxycarbonyl) phenylisoserine 
• 158810-74-3 (-)-(2R,3S)-methyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate 
• 873914-63-7 (4S,5S)-5-(tert-butoxycarbonylamino)-4-hydroxy-5-phenylpentanoic acid ethyl ester 
• 873914-61-5 (2R,3S)-2-[(tert-butyldimethyl-silanyloxy)-3-hydroxy-1-phenylpropyl]-carbamic acid tert-butyl ester 
• 873914-62-6 (4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-5-phenylpent-2-enoic acid ethyl ester 
• 148700-85-0 L 733060 
• 159249-47-5 tert-butyl (2S,3S)-3-hydroxy-2-phenylpiperidine-1-carboxylate 
• 323579-86-8 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-(tert-butyldimethyl-silanyloxy)-3-phenylpropionate 
• 562817-60-1 (2S,3S)-1-(tert-butyloxycarbonyl)-2-phenyl-3-[(3,5)-bis(trifluoromethyl)benzyloxy]piperidine 
• 691871-80-4 (4S,5S)-(2,5-dihydroxy-1-phenylpentyl)-carbamic acid tert-butyl ester 

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.

Synthetic method of paclitaxel side chain

The invention discloses a synthetic method of a paclitaxel side chain. The method comprises the steps of taking (2R, 3S)-3-phenyl isoserine hydrochloride as a raw material; carrying out esterificationreaction under the participation of methanol and thionyl chloride to obtain (2R, 3S)-phenyl isoserine methyl ester; then preparing (2R, 3S)-N-benzoyl-phenyl isoserine methyl ester through a benzoylation reaction; preparing (4S, 5R)-5-methoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-3-benzoyl-1,3-oxazolidine through a cyclization protection reaction; finally, obtaining a paclitaxel side chain crude product through hydrolysis, and further purifying the paclitaxel side chain crude product through recrystallization to obtain a paclitaxel side chain finished product. The method is simple and easy to operate, short in production period, low in cost, high in purification efficiency and suitable for industrial application and market popularization.

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

Syntheses and biological evaluation of C-30-N-acyl modified taxane analogues from 1-deoxybaccatin-VI

A series of side-chain modified taxane analogues were synthesized and their in vitro anticancer activities against four human cancer cell lines: MDA-MB-231 (human breast cancer), PC-3 (human prostatic cancer), HepG2 and H460 (human hepatoma) were studied.

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.

Alkyl 4-chlorobenzoyloxycarbamates as highly effective nitrogen source reagents for the base-free, intermolecular aminohydroxylation reaction

Ethyl-(7), benzyl-(8), tert-butyl-(9), and fluorenylmethyl-4- chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effective under base-free reaction conditions. The scope and limitations of these methods have been explored using a variety of alkenes, among which, trans-cinnamates, in particular, proved to be good substrates.

IMPROVED AMINOHYDROXYLATION OF ALKENES

The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.

Highly diastereoselective enolate addition of O-protected α-hydroxyacetate to (SR)-tert-butanesulfmylimines: Synthesis of taxol side chain

The taxol side chain (sR,2R,3-5)-N-tert-butanesulfinyl-O-Boc-3- phenylisoserine benzyl ester 4c was synthesized through a lithium enolate addition of O-Boc-α-hydroxyacetate benzyl ester 5c to benzylidene (S R)-tert-butanesulfinamide 6a in excellent yield and diastereoselectivity. By similar approach, a series of enantiopure 3-substituted isoserine benzyl esters 4 useful for the semi-syntheses of taxol derivatives were also prepared in high to excellent yields and diastereoselectivities. The diastereoselective addition mechanism was discussed on the basis of the experimental observation.

No auxiliary, no byproduct strategy for water-soluble prodrugs of taxoids: Scope and limitation of O-N intramolecular acyl and acyloxy migration reactions

Since numerous new taxoids active against multidrug resistant (MDR) tumors have been developed and their poor water-solubility is a very real problem in intravenous administration, we have designed and synthesized a series of novel water-soluble taxoid prodrugs (isotaxoids). These prodrugs, a 2′-O-isoform of taxoids, showed promising results with higher water solubility (0.8-1.1 mg/mL) and proper kinetics for parent drug release by a simple pH-dependent chemical mechanism via O-N intramolecular acyl migration. No additional functional auxiliaries are released during the conversion to parent drugs, which would be an advantage in toxicology and general pharmacology, and the cost for the evaluations of auxiliary units in these fields could be saved in prodrug development. In addition, we demonstrate for the first time the successful application of the O-N intramolecular acyloxy migration reaction in the prodrug design, with the exception of the tert-butyloxycarbonyl group, and that this reaction can be provided with no organic solvent and no side products.

A novel method to synthesize docetaxel and its isomer with high yields

Side chains of docetaxel and its isomer were obtained through Staudinger cycloaddition and catalytic hydrogenation of chlorophenyl intermediates, using chlorobenzaldehyde as starting material. Syntheses of three novel chiral azetidinone derivatives through the Staudinger cycloaddition reaction of chlorophenyl chiral amine Schiff base with different substituted positions were described and their ring-opening reaction under the catalysis of Pd/MgCO 3 or Pd/C to afford side chains of docetaxel and its isomer in high yields was investigated. Finally, docetaxel and its isomer were obtained. Single crystal of (3S,4R)-3-hydroxy-N-[(S)(1-phenyl)ethyl]-4 -(2′-chlorophenyl) -2-azetidinone (4c) was obtained, the configuration of which was determined by X-ray diffraction. Because of the mild cyclization reaction condition and convenient asymmetric resolution operation when p-chlorobenzaldehyde was employed instead of benzaldehyde, the yield of cyclization and hydrogenation increased dramatically and the total yield of docetaxel was higher than the result in literature. When o-chlorobenzaldehyde was employed instead of benzaldehyde an isomer of docetaxel was obtained by the same way.