158830-39-8

Basic information

• Product Name: methyl (2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoate
• Synonyms: Cabazitaxel Impurity 46;(2S,3S)-methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate;methyl (2S,3S)-2-hydroxy-3-(N-tert-butoxycarbonylamino)-3-phenylpropanoate;Methyl (2S,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoate;Benzenepropanoic acid, β-[[(1,1-dimethylethoxy)carbonyl]amino]-α-hydroxy-, methyl ester, (αS,βS)-
• CAS NO: 158830-39-8
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.3309
• Mol File: 158830-39-8.mol

Chemical Properties

• Boiling Point: 443.334°C at 760 mmHg
• Flash Point: 221.921°C
• Density: 1.171g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.521
• PKA: 11.22±0.46(Predicted)
• CAS DataBase Reference: methyl (2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoate(158830-39-8)
• EPA Substance Registry System: methyl (2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoate(158830-39-8)

Safety Data

• Hazardous Substances Data: 158830-39-8(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 195196-18-0 (3S,4S)-N-benzyl-4-hydroxy-3-phenylisoxazolidinone 
• 150949-07-8 methyl (2S,3S)-phenylisoserine 
• 129866-71-3 Methyl (2S,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate 
• 150884-50-7 benzaldehyde N-boc imine 
• 126252-53-7 C₁₄H₁₉NO₅ 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 145438-00-2 methyl (+/-)-syn-3-chloro-2-hydroxy-3-phenylpropanoate 
• 145438-00-2 methyl (+/-)-anti-3-chloro-2-hydroxy-3-phenylpropanoate 
• 100-52-7 benzaldehyde 
• 7780-06-5 isopropyl cinnamate 
• 115794-66-6 trans-methyl 3-phenylglycidate 
• 163061-19-6 (2S)-2-tert-butoxycarbonylamino-2-phenylacetaldehyde 

Downstream Products

• 949459-79-4 methyl (4S,5S)-3-(tert-butoxycarbonyl)-2-(p-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-methanoate 
• 342411-13-6 methyl (2R,3S)-2-amino-3-(tert-butoxycarbonylamino)-3-phenylpropionate 
• 342411-11-4 2-azido-3-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 

Relevant articles and documents

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.

Preparation method of paclitaxel oxazole ring side chain intermediate

The invention provides a preparation method of a paclitaxel oxazole ring side chain intermediate, which can effectively enhance the single-step yield, thereby enhancing the total yield of the paclitaxel oxazole ring side chain and lowering the preparation cost. According to the method, suction filtration and concentration are directly carried out on a product (1) in a hydrogenation reduction stepin a process for synthesizing docetaxel by a four-step purification method, the product is used for a subsequent substitution reaction, and the product is subjected to a reaction in an organic solventwith a solvent polarity parameter of less than or equal to 4.5 to prepare a substitution product (2), so that the problem of low yield caused by incomplete extraction during hydrogenation reduction reaction post-treatment is solved.

Dynamic kinetic resolution of α-chloro β-keto esters and phosphonates: Hemisynthesis of Taxotere through Ru-DIFLUORPHOS asymmetric hydrogenation

The dynamic kinetic resolution (DKR) of racemic α-chloro β-ketoesters and α-chloro β-ketophosphonates through ruthenium-mediated asymmetric hydrogenation is reported. The corresponding α-chloro β-hydroxyesters and α-chloro β- hydroxyphosphonates were obtained in good to high enantio- and diastereomeric excesses using, in particular, the atropisomeric ligand DIFLUORPHOS. This methodology allowed an efficient preparation of the anti phenylisoserine side chain of Taxotere which has been used for the hemisynthesis of the cancer therapeutic agent itself. In addition, 13C NMR in chiral oriented solvents was used to investigate the DKR effect.

Acylation of alkyl halides and amino aldehydes with a phosphane oxide-based d1-synthon

Alkyl iodides and α-amino aldehydes can be homologated to the corresponding methyl esters and β-amino methyl esters, including β-amino-α-hydroxy methyl esters, using lithiated (dimethoxymethyl) diphenylphosphane oxide. The primary α,α-(dimethoxy) diphenylphosphane oxides obtained by this Horner-Wittig type process collapse to give the target esters under proton-catalyzed conditions in the presence of water. Detailed and carefully conducted mechanistic studies revealed that the diphenylphosphane oxide group is activated by protonation, and acts as the initial leaving group in this process. In the cases of adducts derived from the reaction of the phosphane oxide-stabilized anion with α-amino aldehydes, homologation to the β-amino- and β-amino-α-hydroxy methyl esters can be achieved by KOtBu-mediated elimination to the intermediate O,O-ketene acetals. These may either be allowed to react with water under acidic conditions to yield the β-amino methyl esters, or may be treated under the Sharpless asymmetric dihydroxylation conditions to directly furnish the β-amino-α-hydroxy methyl esters. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Efficient asymmetric synthesis of 2,3-diamino-3-phenylpropanoic acid derivatives

An efficient, stereoselective synthesis of selectively-protected anti and syn, methyl 2-amino-3-(Boc-amino)-3-phenylpropanoate is described. Preparation of syn β-acetylamino-α-hydroxy ester was from isopropyl cinnamate via an acetamide-based Sharpless ami

Chemoenzymatic synthesis of the C-13 side chain of paclitaxel (Taxol) and docetaxel (Taxotere)

Reduction of methyl 3-chloro-2-oxo-3-phenylpropanoate with various reducing agents gave syn- and anti-3-chloro-2-hydroxy-3-phenylpropanoates 3, which underwent an efficient lipase-catalyzed resolution. All four diastereomers were subsequently converted to N-benzoyl-(2R,3S)-3-phenylisoserine methyl ester, C-13 side chain analogues of paclitaxel (Taxol).

Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O- isopropylidene-D-glyceraldehyde nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine

A remarkable Lewis acid tuning has been observed in the nucleophilic addition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2- O-isopropylidene-D-glyceraldehyde. The obtained α,β-dialkoxy hydroxylamines can serve as starting points for the synthesis of both aminodiols and α- hydroxy-β-amino acids. This synthetic approach is illustrated by the synthesis of the antipode of the C-13 side chain of Taxotere as well as its C-3 epimer.

Totally stereocontrolled nitrone-ketene acetal based synthesis of (2S,3S)-N-benzoyl-and N-boc-phenylisoserine

A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N- benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceeds in up to 59% overall yield and requires only three operations from the starting nitrones.

Method for preparing taxane derivatives

A method for preparing taxane derivatives of general formula (I) by esterifying protected baccatin III or protected 10-deacetyl baccatin III with an acid of general formula (II). In general formulae (I) and (II), Ar is an aryl radical; R1 and R