145514-62-1

Basic information

• Product Name: (2R,3S)-Boc-3-Phenylisoserine
• Synonyms: N-BOC-(2R,3R)-3-AMINO-2-HYDROXY-3-PHENYL-PROPIONIC ACID;(2R,3S)-3-t-butoxy-carbonylamino-2-hydroxy-3-phenylpropionacid;(2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-3-phenylpropion acid;SIDE CHAINS OF DOCETAXEL--4;(2R,3S)-3-(Boc-amino)-2-hydroxy-3-phenyl-propanoic;(2R,3S)-N-Boc-3-Phenyl-isoserine;(2R,3S)-3-t-butoxycarbony-carbonylaMino-2-hydroxy-3-phenylpropinacid;2R,3S)-3-t-butoxy-carbonylaMino-2-hydroxy-3-phenylpropinacid
• CAS NO: 145514-62-1
• Molecular Formula: C₁₄H₁₉NO₅
• Molecular Weight: 281.3
• EINECS: 1806241-263-5
• Mol File: 145514-62-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 470.4oC at 760 mmHg
• Flash Point: 238.3oC
• Appearance: /
• Density: 1.239g/cm3
• Vapor Pressure: 1.19E-09mmHg at 25°C
• Refractive Index: 1.547
• Storage Temp.: -15°C
• PKA: 3.49±0.17(Predicted)
• CAS DataBase Reference: (2R,3S)-Boc-3-Phenylisoserine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-Boc-3-Phenylisoserine(145514-62-1)
• EPA Substance Registry System: (2R,3S)-Boc-3-Phenylisoserine(145514-62-1)

Safety Data

• Hazardous Substances Data: 145514-62-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-white powder

InChI:InChI=1/C14H19NO5/c1-14(2,3)20-13(19)15-10(11(16)12(17)18)9-7-5-4-6-8-9/h4-8,10-11,16H,1-3H3,(H,15,19)(H,17,18)/t10-,11+/m0/s1

Upstream product

• 479078-61-0 (4S,5R)-2-Oxo-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 132201-32-2 (2R,3S)-3-phenylisoserine hydrochloride 
• 124605-42-1 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 1807-69-8 2-diazo-3-oxo-3-phenyl-propionic acid methyl ester 

Downstream Products

• 136561-53-0 (2R,3S)-2-hydroxy-3-amino-3-phenylpropionic acid 
• 188402-08-6 Benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-carboxy-2-phenyl-ethyl ester 
• 655228-34-5 Isobutyric acid (1R,2S)-2-tert-butoxycarbonylamino-1-carboxy-2-phenyl-ethyl ester 
• 655228-35-6 Isobutyric acid (1R,2S)-2-tert-butoxycarbonylamino-1-cyclohexyloxycarbonyl-2-phenyl-ethyl ester 
• 602319-17-5 (1R,2S)-2-[(tert-butoxycarbonyl)amino]-1-[(cyclohexyloxy)carbonyl]-2-phenylethyl benzoate 
• 132201-33-3 (2R,3S)-N-benzoyl-3-phenylisoserine 
• 1013417-71-4 tertiary-butyl (1S,2R)-2-amino-6-(3-tert-butoxycarbonylamino-2-hydroxy-3-phenyl-propionylamino)benzimidazole-1-carboxylate 
• 1013417-11-2 [7-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionylamino)-isoquinolin-1-yl]-N-dicarboxyamino tert-butyl ester 
• 1352243-59-4 C₂₀H₃₀N₂O₆ 
• 1428377-02-9 C₁₉H₂₈N₂O₆ 
• 1428377-03-0 C₁₇H₂₄N₂O₆ 
• 1428377-04-1 C₂₀H₃₀N₂O₆ 
• 1428377-05-2 C₂₂H₂₆N₂O₆ 
• 1428377-06-3 C₂₃H₂₈N₂O₆ 

Relevant articles and documents

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

Design, synthesis and preliminary activity evaluation of novel 3-amino-2-hydroxyl-3-phenylpropanoic acid derivatives as aminopeptidase N/CD13 inhibitors

Aminopeptidase N (APN/CD13) over expressed on tumour cells, plays a critical role in tumour invasion, metastasis and tumour angiogenesis. In this article, we described the design, synthesis and preliminary activity studies of novel 3-amino-2-hydroxyl-3-phenylpropanoic acid derivatives as APN inhibitors. The in vitro enzymatic inhibitions on APN from porcine kidney showed that compound 7e had the most potent inhibitory activity against APN with the IC50 value to 1.26±0.01 μM, which is better than that of bestatin (IC50=2.55±0.11 μM). In addition, compound 7e also showed better inhibitory activity against APN on human ovary clear cell carcinoma cell ES-2 than bestatin with the IC50 value to 30.19±1.02 μM versus 60.61±0.1 μM. Compound 7e could be used as the lead compound in the future for anti-cancer agent research.

Lipase-catalyzed transesterification of methyl 2-substituted 3-hydroxy-4-pentenoates and its synthetic application to the taxol side chain

Syn-and anti-methyl 2-substituted 3-hydroxy-4-pentenoates were efficiently resolved in lipase-catalyzed transesterification. This protocol was successfully applied to the synthesis of the taxol side chain.