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Methyl (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate
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Name

Methyl (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate

 EINECS 608-809-6
CAS No. 32981-85-4 Density 1.236 g/cm3
PSA 75.63000 LogP 2.08250
Solubility N/A Melting Point 178-183℃
Formula C17H17NO4 Boiling Point 540.3 °C at 760 mmHg
Molecular Weight 299.326 Flash Point 280.6 °C
Transport Information N/A Appearance White crystal
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 32981-85-4 (Methyl (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate) Hazard Symbols N/A
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

Article Data 55

Methyl (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate Synthetic route

145041-37-8

methyl (2R,3S)-3-benzoylamino-2-benzyloxy-3-phenylpropanethioate

32981-85-4

methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions
ConditionsYield
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%
99458-15-8

Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate

98-88-4

benzoyl chloride

32981-85-4

methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions
ConditionsYield
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%
146848-86-4

methyl (2R,3S)-2-acetoxy-3-phenyl-3-benzoylaminopropanoate

32981-85-4

methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 1h;92%
146848-91-1

(4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester

32981-85-4

methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions
ConditionsYield
With hydrogenchloride In methanol for 2h; Heating;90%
With hydrogenchloride In methanol for 5h; Heating;85%
With hydrogenchloride In methanol for 5h; Heating;85%
186581-53-3, 908094-01-9

diazomethane

132201-33-3

(2R,3S)-N-benzoyl-3-phenylisoserine

32981-85-4

methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether90%
In methanol; diethyl ether
99458-16-9

(2R,3S)-(+)-methyl 3-azido-2-benzoly-3-phenylpropionate

32981-85-4

methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol88%
With hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal76%
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;
67-56-1

methanol

98-88-4

benzoyl chloride

195624-97-6

(2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester

32981-85-4

methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions
ConditionsYield
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%
67-56-1

methanol

98-88-4

benzoyl chloride

132201-32-2

(2R,3S)-3-phenylisoserine hydrochloride

32981-85-4

methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions
ConditionsYield
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%
67-56-1

methanol

100-44-7

benzyl chloride

195624-97-6

(2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester

32981-85-4

methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions
ConditionsYield
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%
144541-45-7

methyl (2S,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

32981-85-4

methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Conditions
ConditionsYield
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

Methyl (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate Specification

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

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