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
• Article Data: 11

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

• 328402-06-8 (2R,3R)-2-Acetoxy-3-chloro-3-phenyl-propionic acid methyl ester 
• 150884-50-7 benzaldehyde N-boc imine 
• 126252-53-7 C₁₄H₁₉NO₅ 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 14898-52-3 methyl 3-amino-3-phenylpropanoate 
• 195196-19-1 C₄₁H₆₁NO₄Si₂ 
• 195196-15-7 (3S,4S)-4-hydroxy-3-phenyl-N-(1-phenylethyl)isoxazolidinone 
• 100-52-7 benzaldehyde 
• 127001-34-7 N-Benzylidene<(R)-(-)-α-methylbenzyl>amine N-oxide 
• 192764-07-1 N-Benzyl-N-[(S)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methyl]-hydroxylamine 
• 188200-13-7 (2S,3S)-3-(tert-butoxycarbonylamino)-1,2-O-isopropylidene-3-phenyl-1,2-propanediol 
• 165683-83-0 (2S,3S)-3-tert-butoxycarbonylamino-1-tert-butyldimethylsilyloxy-3-phenyl-2-propanol 
• 165683-81-8 (2S,3S)-3-((tert-butoxycarbonyl)amino)-3-phenyl-1,2-propanediol 

Downstream Products

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

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

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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.