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CAS No.: | 32981-85-4 |
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Name: | Methyl (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate |
Article Data: | 55 |
Molecular Structure: | |
Formula: | C17H17NO4 |
Molecular Weight: | 299.326 |
Synonyms: | PACLITAXEL SIDE CHAIN 4;PACLITAXEL SIDE CHAIN NO 4;C-13 SIDE CHAIN FOR PACLITAXEL II;(2R,3S)-1-Benzoyl-2-Hydroxy-3-Aminophenylpionic Acid Ester;METHYL (2R,3S)-3-BENZAMIDO-2-HYDRO-3-PHENYLPROPIONATE;METHYL (2R,3S)-3-BENZAMIDO-2-HYDROXY-3-PHENYLPROPIONATE;N-BENZOYL-(2R,3S)-3-PHENYLISOSERINE METHYL ESTER;PACLITAXE SIDE CHIAN 4 |
EINECS: | 608-809-6 |
Density: | 1.236 g/cm3 |
Melting Point: | 178-183℃ |
Boiling Point: | 540.3 °C at 760 mmHg |
Flash Point: | 280.6 °C |
Appearance: | White crystal |
PSA: | 75.63000 |
LogP: | 2.08250 |
methyl (2R,3S)-3-benzoylamino-2-benzyloxy-3-phenylpropanethioate
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate
Conditions | Yield |
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With palladium on activated charcoal; hydrogen In methanol under 4654.46 Torr; | 100% |
With hydrogen; 1% Pd/C In methanol under 4654.46 Torr; | 100% |
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol at 60℃; for 1h; | 78% |
With hydrogen; palladium on activated charcoal In ethanol at 60℃; | 78% |
Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate
benzoyl chloride
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate
Conditions | Yield |
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Stage #1: Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate; benzoyl chloride With dmap; triethylamine In ethyl acetate at 20℃; for 4h; Stage #2: With hydrogen; palladium on activated charcoal In methanol; ethyl acetate for 48h; Further stages.; | 92% |
Stage #1: Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate; benzoyl chloride With dmap; triethylamine In methanol; ethyl acetate at 20℃; for 7h; Stage #2: With hydrogen; palladium on activated carbon In methanol; ethyl acetate for 48h; | 92% |
Stage #1: Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate; benzoyl chloride; dmap In methanol; ethyl acetate at 20℃; for 7h; Stage #2: With hydrogen; palladium 10% on activated carbon In methanol; ethyl acetate for 48h; | 88% |
methyl (2R,3S)-2-acetoxy-3-phenyl-3-benzoylaminopropanoate
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate
Conditions | Yield |
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With sodium methylate In methanol at 20℃; for 1h; | 92% |
(4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 2h; Heating; | 90% |
With hydrogenchloride In methanol for 5h; Heating; | 85% |
With hydrogenchloride In methanol for 5h; Heating; | 85% |
diazomethane
(2R,3S)-N-benzoyl-3-phenylisoserine
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether | 90% |
In methanol; diethyl ether |
(2R,3S)-(+)-methyl 3-azido-2-benzoly-3-phenylpropionate
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol | 88% |
With hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal | 76% |
With hydrogen; palladium on activated charcoal In methanol under 2585.7 Torr; for 4h; | 74% |
With hydrogen; palladium on activated charcoal In methanol at 20℃; under 760 Torr; for 48h; | 71% |
With hydrogen; palladium on activated charcoal 1.) CH3OH, 15 h, 2.) CH3OH, RT, 72 h; Yield given. Multistep reaction; |
methanol
benzoyl chloride
(2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate
Conditions | Yield |
---|---|
Stage #1: methanol; (2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester With hydrogenchloride for 20h; Heating; Stage #2: benzoyl chloride With triethylamine In dichloromethane at 0 - 20℃; | 88% |
methanol
benzoyl chloride
(2R,3S)-3-phenylisoserine hydrochloride
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate
Conditions | Yield |
---|---|
Stage #1: benzoyl chloride; (2R,3S)-3-phenylisoserine hydrochloride With sodium hydroxide In water at 20℃; for 1h; pH=9 - 12; Stage #2: methanol Concentration; | 85.6% |
methanol
benzyl chloride
(2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate
Conditions | Yield |
---|---|
Stage #1: methanol; (2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester With hydrogenchloride for 20h; Addition; Heating; Stage #2: benzyl chloride With triethylamine In dichloromethane at 0 - 20℃; for 2h; Substitution; Further stages.; | 85% |
methyl (2S,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate
Conditions | Yield |
---|---|
With thionyl chloride In dichloromethane for 5h; Inert atmosphere; Reflux; | 85% |
Multi-step reaction with 2 steps 1.1: SOCl2 / CH2Cl2 / Heating 2.1: HCl / H2O; methanol / Heating 2.2: NaHCO3 / H2O; methanol / 50 °C View Scheme | |
Multi-step reaction with 2 steps 1: 90 percent / DEAD; PPh3 / benzene / 20 h / 20 °C 2: 90 percent / 1N aq. HCl / methanol / 2 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 77 percent / Ph3P, diethylazodicarboxylate / tetrahydrofuran / Ambient temperature 2: 1.) aq. HCl, 2.) aq. NaHCO3 / 1) CH3OH, room temperature, 1.5 h; 2) room temperature, 16 h View Scheme | |
Multi-step reaction with 2 steps 1: 1) SOCl2 / 1) CHCl3, 45 deg C, 5 h, 2) CHCl3, reflux, 48 h 2: 80 percent / 1N HCl / methanol / 2 h / Heating View Scheme |
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The CAS registry number of Benzenepropanoicacid, b-(benzoylamino)-a-hydroxy-, methyl ester, (aR,bS)- is 32981-85-4. The IUPAC name is methyl (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate. In addition, the molecula formula is C17H17NO4 and the molecular weight is 299.32. It belongs to the classes of Chiral Chemicals and Intermediates. It is a kind of white crystal powder.
Physical properties about Benzenepropanoicacid, b-(benzoylamino)-a-hydroxy-, methyl ester, (aR,bS)- are: (1)ACD/LogP: 2.90; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.9; (4)ACD/LogD (pH 7.4): 2.9; (5)ACD/BCF (pH 5.5): 94.35; (6)ACD/BCF (pH 7.4): 94.34; (7)ACD/KOC (pH 5.5): 901.82; (8)ACD/KOC (pH 7.4): 901.8; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 55.84 Å2; (13)Index of Refraction: 1.588; (14)Molar Refractivity: 81.53 cm3; (15)Molar Volume: 242.1 cm3; (16)Polarizability: 32.32 ×10-24cm3; (17)Surface Tension: 51.7 dyne/cm; (18)Density: 1.236 g/cm3; (19)Flash Point: 280.6 °C; (20)Enthalpy of Vaporization: 86.08 kJ/mol; (21)Boiling Point: 540.3 °C at 760 mmHg; (22)Vapour Pressure: 1.66E-12 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)[C@H](O)[C@@H](NC(=O)c1ccccc1)c2ccccc2
(2)InChI: InChI=1/C17H17NO4/c1-22-17(21)15(19)14(12-8-4-2-5-9-12)18-16(20)13-10-6-3-7-11-13/h2-11,14-15,19H,1H3,(H,18,20)/t14-,15+/m0/s1
(3)InChIKey: UYJLJICUXJPKTB-LSDHHAIUBE