124605-42-1

Basic information

• Product Name: Methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate
• Synonyms: (2R,3S)-2-HYDROXY-3-(N-TERTBUTOXYCARBONYL) AMINO-3- PHENYL- METHYL PROPIONATE (INTERMEDIATE OF DOCETAXEL);(2R,3S)-2-Hydroxy-3-(N-tert.-Butyoxycarbonyl)amino-3-Phenylmethylpropionate;(2R,3S)-N-TERT-BUTOXYCARBONYL 3-PHENYLISOSERINE METHYL ESTER,98+%;BENZENEPROPANOICACID,B-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-A-HYDROXY-,METHYLESTER;(2R,3S)-N-t-Butoxycarbonyl-3-phenylisoserine methyl ester, (2R,3S)-2-Hydroxy-3-(N-t-butyloxycarbonyl)amino-3-phenylmethyl propionate, ee >99%;Boc-RS-iSer(3-Ph)-OMe;(2R,3S)-N-tert-butoxycarbony-3-phenylisoserine methyl ester;METHYL (2R,3S)-N-BOC-3-PHENYL ISOSERINE
• CAS NO: 124605-42-1
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.33
• EINECS: 1806241-263-5
• Mol File: 124605-42-1.mol

Chemical Properties

• Melting Point: 132-133°C
• Boiling Point: 443.334 °C at 760 mmHg
• Flash Point: 221.921 °C
• Appearance: /
• Density: 1.170
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.521
• Storage Temp.: 2-8°C
• PKA: 11.22±0.46(Predicted)
• CAS DataBase Reference: Methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate(124605-42-1)
• EPA Substance Registry System: Methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate(124605-42-1)

Safety Data

• Hazardous Substances Data: 124605-42-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate is used as a key intermediate in the synthesis of taxol and its derivatives. Taxol, a widely used chemotherapy drug, is effective against various types of cancer, including ovarian, breast, lung, and Kaposi's sarcoma. The compound plays a crucial role in the development of new and improved cancer treatments by facilitating the production of taxol and its analogs.
Used in Chemical Research:
As a versatile organic compound, Methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate is also used in various chemical research applications. It can be employed as a starting material or a building block for the synthesis of other complex organic molecules, contributing to the advancement of chemical science and the development of new pharmaceuticals, materials, and other specialty chemicals.

InChI:InChI=1/C15H21NO5/c1-15(2,3)21-14(19)16-11(12(17)13(18)20-4)10-8-6-5-7-9-10/h5-9,11-12,17H,1-4H3,(H,16,19)/t11-,12+/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 99458-15-8 Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate 
• 157240-36-3 (2R,3S)-3-phenylisoserine methyl ester 
• 154136-25-1 methyl (2R,3S)-2-benzyloxy-3-tert-butoxycarbonylamino-3-phenylpropanoate 
• 158807-51-3 (R)-3-tert-butoxycarbonylamino-3-phenylpropionic acid methyl ester 
• 73210-14-7 N-chloro-N-sodio-tert-butylcarbamate 
• 103-26-4 Methyl cinnamate 
• 203806-61-5 (2R,3S)-3-tert-Butoxycarbonylamino-3-phenyl-2-triisopropylsilanyloxy-propionic acid methyl ester 
• 4248-19-5 tert-butyl carbazate 
• 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 
• 7780-06-5 isopropyl cinnamate 
• 32803-73-9 methyl 3-phenyl-3-chloro-2-ketopropionate 

Downstream Products

• 153652-71-2 (4S,5R)-2,2-Dimethyl-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester 
• 157580-28-4 (2R,4S,5R)-2-(3,4-Dimethoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester 
• 157580-26-2 (2R,4S,5R)-2,4-Diphenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester 
• 153652-75-6 (2S,4S,5R)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester 
• 153652-73-4 (2R,4S,5R)-3-t-butoxycarbonyl-4-phenyl-2-(4-methoxyphenyl)-5-methoxycarbonyl-1,3-oxazolidine 
• 274681-92-4 methyl (2S,3S)-2-azido-3-(tert-butoxycarbonylamino)-3-phenylpropionate 
• 323579-86-8 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-(tert-butyldimethyl-silanyloxy)-3-phenylpropionate 
• 670254-71-4 (2*,4S,5R)-methyl N-tert-butoxycarbonyl-2-(4'-methoxy)phenyl-4-phenyl-1,3-oxazolidine-5-methionate 
• 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 

Relevant articles and documents

Asymmetric synthesis of taxol and taxotere side chains by enolate hydroxylation

We report an asymmetric synthesis of the taxol and taxotere side chains by hydroxylation of enolates derived from N-substituted methyl 3-amino-3-phenyl propionate with the oxodiperoxymolybdenum (pyridine) (hexamethyl phosphoric triamide) complex (MoOPH). We report an asymmetric synthesis of the taxol and taxotere side chains by hydroxylation of enolates derived from N-substituted methyl 3-amino-3-phenyl propionate with the oxodiperoxymolybdenum (pyridine) (hexamethyl phosphoric triamide) complex (MoOPH).

Preparation method of docetaxel chiral side chain intermediate

The invention discloses a preparation method of a docetaxel chiral side chain intermediate. The method takes cheap and easily available L-phenylglycine 1 as a raw material, and the route is convenient to operate, good in stereoselectivity, mild in reaction condition, simple to separate and purify and relatively high in total yield, and can be used for large-scale preparation. The adopted raw materials are non-toxic, the production process is pollution-free and environment-friendly, and good conditions are created for industrial large-scale production and commercialization of the product.

Synthetic method of docetaxel side chain

The invention relates to a synthetic method of a docetaxel side chain, which comprises the following steps: by using (2R, 3S)-2-hydroxy-3-phenyl-3-(((S)-1-phenethyl)-amino)methyl propionate as a raw material, carrying out reduction reaction in the presence of palladium on carbon and hydrogen to obtain (2R, 3S)-3-phenyl isoserine methyl ester salt, and carrying out di-tert-butyl dicarbonate substitution reaction to obtain (2R, 3S)-3-t-butyloxycarboryl-2-hydroxy-3-Methyl 3-phenylpropionate; preparing (4S, 5R)-3-tert-butoxycarbonyl-2-(4-methoxy phenyl)-4-phenyl-5-oxazoline carboxylic acid methylester from through cyclization protection reaction, and finally hydrolyzing to obtain a docetaxel side chain crude product; and recrystallizing the crude product of the docetaxel side chain, and further purifying to obtain a finished product of the docetaxel side chain. The synthetic method disclosed by the invention is safe, environment-friendly, economical, efficient and suitable for large-scaleindustrial production.

3-phenylisoserine derivative production method

The present invention provides a 3-phenylisoserine derivative production method for obtaining 3-phenylisoserine derivatives represented by formula (2) (in the formula, R1 represents a phenyl group or a phenyl group having a substituent group; R3 represents a hydrogen atom, a methyl group, a benzyl group, a p-methoxybenzyl group, a tert-butly group, a methoxymethyl group, a 2-tetrahydropyranyl group, an ethoxyethyl group, an acetyl group, a pivoloyl group, a benzoyl group, a trimethylsilyl group, a triethylsilyl group, or a tert-butyldimethylsilyl group; R4 represents a formyl group, an acetyl group, a benzoyl group, a tert-butoxycarbonyl group, or a benzyloxycarbonyl group; and R5 represents a C1-4 alkyl group) by protecting, in water or a mixed solvent containing water, the amino group of a compound represented by formula (1) (in the formula, R1 represents a phenyl group or a phenyl group having a substituent group; R2 represents an alkali metal, an alkaline earth metal, or a nitrogenous base; and R3 represents a hydrogen atom, a methly group, a benzyl group, a p-methoxybenzyl group, a tert-butyl group, a methoxymethyl group, a 2-tetrahydropyranyl group, an ethoxymethly group, an acetyl group, a pivoloyl group, a benzoyl group, a trimethylsilyl group, a triethylsilyl group, or a tert-butyldimethylsilyl group), and when a specific compound has been obtained, extracting the compound using a C4 ether solvent, and while removing the C4 ether solvent and moisture content, replacing at least some of the C4 ether solvent with a C1-4 aliphatic alcohol and implementing an esterification reaction, and then isolating the 3-phenylisoserine derivative at 0-30 DEG C. The 3-phenylisoserine derivative production method enables the production of 3-phenylisoserine derivatives having at least 99% purity.

Docetaxel side chain 2'-derived novel taxanes antitumor compound as well as synthesis method and application thereof

The invention discloses a docetaxel side chain 2'-derived novel taxanes antitumor compound shown as the general structure formula (I) as well as a synthesis method and application thereof. In the formula, X is N or O, R is H or acetyl, and R' is H, nitryl, cyano, methoxyl or a halogen group. The synthesis method takes 10-deacetylbaccatin is used as a raw material; after 7-OH and 10-OH are protected, condensation with phenylisoserine (side chain) protecting 3'-NHBoc and 2'-OH in the presence of condensation agents DCC (Dicyclohexylcarbodiimide) and DMAP (Dimethylaminopyridine) is performed; esterification with substituted phenyl isoxazole carboxylic acid or substituted phenyl oxadiazole methyl carboxylic acid in the presence of the DCC and the DMAP is performed; finally, a protecting group is removed to obtain the compound. The compound disclosed by the invention has relatively high activity on tumor cells.

Novel taxane anti-tumor compound as well as synthesis method and application thereof

The invention discloses a novel taxane anti-tumor compound shown in a structural formula (I). 10-DAB (10-deacetylbaccatin) is adopted as a raw material, and is condensed with phenylisoserine (side chain) with protected 3'-NH2 and 2'-OH in the presence of condensing agents DCC and DMAP after 7-OH and 10-OH are protected, the side chain and a protecting group on a baccatin ring are simultaneously removed in the presence of zinc powder, and coupling is performed with substituted phenylisoxazole in an alkaline medium to obtain a target product. The compound has relatively high anti-tumor activity. (The structural formula (I) is shown in the description.).

Stereoselective synthesis of 4-substituted-cyclic sulfamidate-5-carboxylates by asymmetric transfer hydrogenation accompanied by dynamic kinetic resolution and applications to concise stereoselective syntheses of (-)-epi-cytoxazone and the taxotere side-c

Dynamic kinetic resolution driven, asymmetric transfer hydrogenation reactions of cyclic sulfamidate imine-5-carboxylate esters were developed. Applications of the new methodology to stereoselective syntheses of the taxotere side-chain and (-)-epi-cytoxaz

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.

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.

PREPARATION OF β-PHENYL-ISOSERINE DERIVATIVES

A process for stereoselective synthesis of a β-phenylisoserine comprises reacting a carbonyl imine R-C=N-CO-OR1 with a protected α- oxyaldehyde X1O-CH2CHO in the presence of a chiral amine catalyst and oxidizing aldehyde s