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(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyric acid

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Name

(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyric acid

EINECS 1308068-626-2
CAS No. 59554-14-2 Density 1.285 g/cm3
PSA 83.55000 LogP 0.70220
Solubility N/A Melting Point 235-237 °C (decomp)
Formula C10H13NO3 Boiling Point 428.5 °C at 760 mmHg
Molecular Weight 195.218 Flash Point 213 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 59554-14-2 (3-AMINO-2-HYDROXY-4-PHENYLBUTYRIC ACID) Hazard Symbols N/A
Synonyms

Benzenebutanoicacid, b-amino-a-hydroxy-, [S-(R*,S*)]-;(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoic acid;(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyricacid;

Article Data 14

(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyric acid Synthetic route

130115-05-8

(2S,3R)-3-Amino-2-hydroxy-4-phenyl-butyric acid isopropyl ester

59554-14-2

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid

Conditions
ConditionsYield
With hydrogenchloride; ion exchange resin (H+) 1.) 4 h, 100 deg C;85%
180922-44-5

(2S,3R)-2-hydroxy-4-phenyl-3-(tosylamino)butanoic acid

59554-14-2

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid

Conditions
ConditionsYield
With Na-naphthalide In 1,2-dimethoxyethane at -78℃; for 0.5h;82%
59969-65-2

(2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenyl-butanoic acid

59554-14-2

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid

Conditions
ConditionsYield
With hydrogen; palladium
95832-38-5

methyl (4R,5S)-2-oxo-4-phenylmethyl-1,3-oxazolidine-5-carboxylate

59554-14-2

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid

Conditions
ConditionsYield
With lithium hydroxide In methanol; water
114886-83-8

methyl (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoate

59554-14-2

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid

Conditions
ConditionsYield
With hydrogenchloride
577978-91-7

(2S,3R)-2-O-benzyl-4-phenyl-3-[(9-phenyl-9-fluorenyl)-amino]-phenylbutanoic acid

59554-14-2

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol at 70℃; for 12h;
121445-52-1

(2S,3R)-3-azido-2-hydroxy-4-phenylbutanoic acid

59554-14-2

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid

Conditions
ConditionsYield
With sodium tetrahydroborate; copper(II) nitrate In water at 0℃; for 0.5h;
869103-47-9

(4S,5R)-4,5-dihydro-2-phenyl-4-carboethoxy-5-benzyl-1,3-oxazole

59554-14-2

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water for 8h; Heating;
869103-46-8

ethyl (2R,3S)-4-phenyl-2,3-oxiranebutanoate

59554-14-2

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 78 percent / BF3*Et2O / 0 - 20 °C
2: hydrochloric acid / H2O; ethanol / 8 h / Heating
View Scheme
718-08-1

ethyl 3-oxo-4-phenylbutyrate

59554-14-2

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 92 percent / sulfuryl chloride / CHCl3 / 20 °C
2: 82 percent / Escherichia coli BL21(DE3)(pIK4) overexpressing reductase; glucose; air / KPi buffer; XAD-4 resin / 24 h / 30 °C / pH 5.6
3: 99 percent / potassium carbonate / H2O; dimethylformamide / 5 h / 20 °C
4: 78 percent / BF3*Et2O / 0 - 20 °C
5: hydrochloric acid / H2O; ethanol / 8 h / Heating
View Scheme

(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyric acid Specification

The cas register number of (2S,3R)-3-Amino-2-hydroxy-4-phenylbutyric acid is 59554-14-2. It also can be called as Benzenebutanoic acid, b-amino-a-hydroxy-, (aS,bR)- and the Systematic name about this chemical is 3-amino-2-hydroxy-4-phenylbutanoic acid.

Physical properties about (2S,3R)-3-Amino-2-hydroxy-4-phenylbutyric acid are: (1)ACD/LogP: 1.36; (2)ACD/LogD (pH 5.5): -1.14; (3)ACD/LogD (pH 7.4): -1.14; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 4; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 6; (11)Polar Surface Area: 38.77Å2; (12)Index of Refraction: 1.595; (13)Molar Refractivity: 51.61 cm3; (14)Molar Volume: 151.8 cm3; (15)Polarizability: 20.46x10-24cm3; (16)Surface Tension: 61.8 dyne/cm; (17)Enthalpy of Vaporization: 72.07 kJ/mol; (18)Vapour Pressure: 4.17E-08 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)C(O)C(N)Cc1ccccc1
(2)InChI: InChI=1/C10H13NO3/c11-8(9(12)10(13)14)6-7-4-2-1-3-5-7/h1-5,8-9,12H,6,11H2,(H,13,14)
(3)InChIKey: LDSJMFGYNFIFRK-UHFFFAOYAX
(4)Std. InChI: InChI=1S/C10H13NO3/c11-8(9(12)10(13)14)6-7-4-2-1-3-5-7/h1-5,8-9,12H,6,11H2,(H,13,14)
(5)Std. InChIKey: LDSJMFGYNFIFRK-UHFFFAOYSA-N

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