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
• Article Data: 30

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

Chemical Properties

off-white crystal powde

Uses

(2R,3S)-N-Boc-3-Phenylisoserine Methyl Ester is used in preparation of taxol oxazole ring side chain intermediates.

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 
• 140-10-3 (E)-3-phenylacrylic acid 
• 60512-85-8 (E)-isopropyl cinnamate 
• 7440-05-3 palladium 
• 2935-35-5 (S)-2-phenylglycine 
• 67-56-1 methanol 
• 132201-32-2 (2R,3S)-3-phenylisoserine hydrochloride 
• 1807-69-8 2-diazo-3-oxo-3-phenyl-propionic acid methyl ester 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 126252-53-7 C₁₄H₁₉NO₅ 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 150884-50-7 benzaldehyde N-boc imine 

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 
• 274681-94-6 methyl (2S,3S)-2-amino-3-[(tert-butoxycarbonyl)amino]-3-phenylpropanoate 
• 153652-73-4 (2R,4S,5R)-3-t-butoxycarbonyl-4-phenyl-2-(4-methoxyphenyl)-5-methoxycarbonyl-1,3-oxazolidine 
• 145514-62-1 RPR 130523 
• 153652-75-6 (2S,4S,5R)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester 
• 114915-14-9 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel 
• 859498-31-0 C₅₇H₆₁Cl₆NO₁₉ 
• 1246748-59-3 C₆₆H₇₃NO₁₆Si 
• 1246748-58-2 C₆₆H₇₅NO₁₆Si 
• 125354-16-7 10-acetyldocetaxel 
• 1033962-75-2 (2R,4S,5R)-2-(1'-naphthyl)-3-t-butoxycarbonyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid methyl ester 
• 238413-40-6 (4S,5R)-3-t-butoxycarbonyl-2-(2,4-dimethoxyphenyl)-4-phenyl-5-methoxycarbonyl-1,3-oxazolidine 
• 202741-88-6 (4S,5R)-4-phenyl-2-trichloromethyl-1,3-oxazolidine-5-carboxylic acid 

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).

Chiral calcium iodide for asymmetric mannich-type reactions of malonates with imines providing β-aminocarbonyl compounds

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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.

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.).