Product Name

  • Name

    3-AMINO-2-HYDROXY-4-PHENYLBUTYRIC ACID

  • EINECS 1308068-626-2
  • CAS No. 59554-14-2
  • Article Data14
  • CAS DataBase
  • Density 1.285 g/cm3
  • Solubility
  • 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
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 59554-14-2 (3-AMINO-2-HYDROXY-4-PHENYLBUTYRIC ACID)
  • Hazard Symbols
  • 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;
  • PSA 83.55000
  • LogP 0.70220

Synthetic route

(2S,3R)-3-Amino-2-hydroxy-4-phenyl-butyric acid isopropyl ester
130115-05-8

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

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
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%
(2S,3R)-2-hydroxy-4-phenyl-3-(tosylamino)butanoic acid
180922-44-5

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

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic 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%
(2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenyl-butanoic acid
59969-65-2

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

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
With hydrogen; palladium
methyl (4R,5S)-2-oxo-4-phenylmethyl-1,3-oxazolidine-5-carboxylate
95832-38-5

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

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
With lithium hydroxide In methanol; water
methyl (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoate
114886-83-8

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

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
With hydrogenchloride
(2S,3R)-2-O-benzyl-4-phenyl-3-[(9-phenyl-9-fluorenyl)-amino]-phenylbutanoic acid
577978-91-7

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

(2S,3R)-3-amino-2-hydroxy-4-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;
(2S,3R)-3-azido-2-hydroxy-4-phenylbutanoic acid
121445-52-1

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

(2S,3R)-3-amino-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;
(4S,5R)-4,5-dihydro-2-phenyl-4-carboethoxy-5-benzyl-1,3-oxazole
869103-47-9

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

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water for 8h; Heating;
ethyl (2R,3S)-4-phenyl-2,3-oxiranebutanoate
869103-46-8

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

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
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
ethyl 3-oxo-4-phenylbutyrate
718-08-1

ethyl 3-oxo-4-phenylbutyrate

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
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
ethyl 2-chloro-3-oxo-4-phenylbutyrate
444613-61-0

ethyl 2-chloro-3-oxo-4-phenylbutyrate

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 82 percent / Escherichia coli BL21(DE3)(pIK4) overexpressing reductase; glucose; air / KPi buffer; XAD-4 resin / 24 h / 30 °C / pH 5.6
2: 99 percent / potassium carbonate / H2O; dimethylformamide / 5 h / 20 °C
3: 78 percent / BF3*Et2O / 0 - 20 °C
4: hydrochloric acid / H2O; ethanol / 8 h / Heating
View Scheme
ethyl (2R,3S)-2-chloro-3-hydroxy-4-phenylbutyrate
832110-38-0

ethyl (2R,3S)-2-chloro-3-hydroxy-4-phenylbutyrate

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 99 percent / potassium carbonate / H2O; dimethylformamide / 5 h / 20 °C
2: 78 percent / BF3*Et2O / 0 - 20 °C
3: hydrochloric acid / H2O; ethanol / 8 h / Heating
View Scheme
(Z)-4-phenylbut-2-en-1-ol
22910-59-4

(Z)-4-phenylbut-2-en-1-ol

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: periodic acid; RuCl3
2: NaN3 / Cu(NO3)2 / H2O / 1.5 h / 65 °C
3: NaBH4 / Cu(NO3)2 / H2O / 0.5 h / 0 °C
View Scheme
(2R,3S)-2-Hydroxymethyl-3-phenylmethyloxirane
161170-91-8

(2R,3S)-2-Hydroxymethyl-3-phenylmethyloxirane

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: periodic acid; RuCl3
2: NaN3 / Cu(NO3)2 / H2O / 1.5 h / 65 °C
3: NaBH4 / Cu(NO3)2 / H2O / 0.5 h / 0 °C
View Scheme
(2S,3S)-3-Benzyl-oxirane-2-carboxylic acid
608520-03-2

(2S,3S)-3-Benzyl-oxirane-2-carboxylic acid

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaN3 / Cu(NO3)2 / H2O / 1.5 h / 65 °C
2: NaBH4 / Cu(NO3)2 / H2O / 0.5 h / 0 °C
View Scheme
methyl (2S,3R)-2-methoxy-4-phenyl-3-<(R)-1-phenylethylamino>butanoate
246522-99-6

methyl (2S,3R)-2-methoxy-4-phenyl-3-<(R)-1-phenylethylamino>butanoate

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 81 percent / BBr3 / CH2Cl2 / 2 h / -78 °C
2: 79 percent / H2 / Pd/C / methanol / 15 h / Ambient temperature
3: 2 N aq. HCl
View Scheme
methyl (2S,3R)-2-hydroxy-4-phenyl-3-<(R)-1-phenylethylamino>butanoate
246523-03-5

methyl (2S,3R)-2-hydroxy-4-phenyl-3-<(R)-1-phenylethylamino>butanoate

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 79 percent / H2 / Pd/C / methanol / 15 h / Ambient temperature
2: 2 N aq. HCl
View Scheme
ethyl (2S,3R)-2-hydroxy-4-phenyl-3-(tosylamino)butanoate
180922-42-3

ethyl (2S,3R)-2-hydroxy-4-phenyl-3-(tosylamino)butanoate

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84 percent / K2CO3 / methanol; H2O / 24 h / Ambient temperature
2: 82 percent / Na-naphthalide / 1,2-dimethoxy-ethane / 0.5 h / -78 °C
View Scheme
(4R,5S)-5-benzyl-4-(hydroxymethyl)-1,3-oxazolidin-2-one
95832-37-4

(4R,5S)-5-benzyl-4-(hydroxymethyl)-1,3-oxazolidin-2-one

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 2N LiOH / methanol; H2O
View Scheme
N-<(benzyloxy)carbonyl>-(2R)-amino-1-phenylbut-3-ene
95832-30-7

N-<(benzyloxy)carbonyl>-(2R)-amino-1-phenylbut-3-ene

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 95 percent / KH / dimethylformamide; benzene
2: 80 percent / I2
3: 1.) AgOAc, 2.) 1N NaOH / 1.) DMF, AcOH, 2.)MeOH, H2O
4: 82 percent / Na / NH3
6: 2N LiOH / methanol; H2O
View Scheme
(4R,5S)-3,4-Dibenzyl-5-hydroxymethyl-oxazolidin-2-one
95891-28-4

(4R,5S)-3,4-Dibenzyl-5-hydroxymethyl-oxazolidin-2-one

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 82 percent / Na / NH3
3: 2N LiOH / methanol; H2O
View Scheme
Z-D-phenylalanine ethyl ester
95832-31-8

Z-D-phenylalanine ethyl ester

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1.) DIBAH, 2.) KH / 1.) toluene, 2.) toluene and THF
2: 95 percent / KH / dimethylformamide; benzene
3: 80 percent / I2
4: 1.) AgOAc, 2.) 1N NaOH / 1.) DMF, AcOH, 2.)MeOH, H2O
5: 82 percent / Na / NH3
7: 2N LiOH / methanol; H2O
View Scheme
Benzyl-((R)-1-benzyl-allyl)-carbamic acid benzyl ester
95832-34-1

Benzyl-((R)-1-benzyl-allyl)-carbamic acid benzyl ester

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 80 percent / I2
2: 1.) AgOAc, 2.) 1N NaOH / 1.) DMF, AcOH, 2.)MeOH, H2O
3: 82 percent / Na / NH3
5: 2N LiOH / methanol; H2O
View Scheme
(4R,5S)-3,4-Dibenzyl-5-iodomethyl-oxazolidin-2-one
95832-35-2

(4R,5S)-3,4-Dibenzyl-5-iodomethyl-oxazolidin-2-one

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) AgOAc, 2.) 1N NaOH / 1.) DMF, AcOH, 2.)MeOH, H2O
2: 82 percent / Na / NH3
4: 2N LiOH / methanol; H2O
View Scheme
(S)-Methyl mandelate
21210-43-5

(S)-Methyl mandelate

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 93 percent / ImH / dimethylformamide / Ambient temperature
2: 80 percent / DIBAL / diethyl ether; hexane / 0.33 h / -78 °C
3: 100 percent / anhyd. MgSO4 / toluene / 0.83 h / 0 °C
4: NEt3 / CH2Cl2 / Ambient temperature
5: 70 percent / HCl
6: 93 percent / pyridine / CH2Cl2 / 0.17 h / 0 °C
7: 92 percent / H2 / 10percent Pd/C / ethyl acetate / Ambient temperature
8: 85 percent / 1.) 6 M HCl, 2.) ion exchange resin (H+) / 1.) 4 h, 100 deg C
View Scheme
(2S)-2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde
133187-22-1

(2S)-2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 100 percent / anhyd. MgSO4 / toluene / 0.83 h / 0 °C
2: NEt3 / CH2Cl2 / Ambient temperature
3: 70 percent / HCl
4: 93 percent / pyridine / CH2Cl2 / 0.17 h / 0 °C
5: 92 percent / H2 / 10percent Pd/C / ethyl acetate / Ambient temperature
6: 85 percent / 1.) 6 M HCl, 2.) ion exchange resin (H+) / 1.) 4 h, 100 deg C
View Scheme
Methyl (S)-(+)-α-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-α-phenylacetate
133187-21-0

Methyl (S)-(+)-α-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-α-phenylacetate

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 80 percent / DIBAL / diethyl ether; hexane / 0.33 h / -78 °C
2: 100 percent / anhyd. MgSO4 / toluene / 0.83 h / 0 °C
3: NEt3 / CH2Cl2 / Ambient temperature
4: 70 percent / HCl
5: 93 percent / pyridine / CH2Cl2 / 0.17 h / 0 °C
6: 92 percent / H2 / 10percent Pd/C / ethyl acetate / Ambient temperature
7: 85 percent / 1.) 6 M HCl, 2.) ion exchange resin (H+) / 1.) 4 h, 100 deg C
View Scheme
(2S,3R,4S)-3-Amino-2-benzyloxy-4-hydroxy-4-phenyl-butyric acid isopropyl ester
130115-10-5, 139630-60-7

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

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 93 percent / pyridine / CH2Cl2 / 0.17 h / 0 °C
2: 92 percent / H2 / 10percent Pd/C / ethyl acetate / Ambient temperature
3: 85 percent / 1.) 6 M HCl, 2.) ion exchange resin (H+) / 1.) 4 h, 100 deg C
View Scheme
[Bis-(4-methoxy-phenyl)-methyl]-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-eth-(E)-ylidene]-amine
139580-07-7

[Bis-(4-methoxy-phenyl)-methyl]-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-eth-(E)-ylidene]-amine

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: NEt3 / CH2Cl2 / Ambient temperature
2: 70 percent / HCl
3: 93 percent / pyridine / CH2Cl2 / 0.17 h / 0 °C
4: 92 percent / H2 / 10percent Pd/C / ethyl acetate / Ambient temperature
5: 85 percent / 1.) 6 M HCl, 2.) ion exchange resin (H+) / 1.) 4 h, 100 deg C
View Scheme
methanol
67-56-1

methanol

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

(2S,3R)-3-Amino-2-hydroxy-4-phenyl-butyric acid methyl ester; hydrochloride

(2S,3R)-3-Amino-2-hydroxy-4-phenyl-butyric acid methyl ester; hydrochloride

Conditions
ConditionsYield
With chloro-trimethyl-silane Heating;100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

(2S,3R)-3-[(tert-butoxycarbonyl) amino]-2-hydroxy-4-phenyl-butanoic acid
62023-65-8

(2S,3R)-3-[(tert-butoxycarbonyl) amino]-2-hydroxy-4-phenyl-butanoic acid

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; for 1h;100%
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 24h;99%
With triethylamine In tetrahydrofuran; water at 10 - 25℃; Cooling with ice;81%
(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Fmoc AHPA

Fmoc AHPA

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; for 1h;100%
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

benzyl chloroformate
501-53-1

benzyl chloroformate

(2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenyl-butanoic acid
59969-65-2

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

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran at 20℃; for 6h; Cooling with ice;64%
With sodium hydroxide In diethyl ether; water Yield given;
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

Carbonic acid tert-butyl ester 4,5-dimethyl-pyrimidin-2-yl ester

Carbonic acid tert-butyl ester 4,5-dimethyl-pyrimidin-2-yl ester

(2S,3R)-3-[(tert-butoxycarbonyl) amino]-2-hydroxy-4-phenyl-butanoic acid
62023-65-8

(2S,3R)-3-[(tert-butoxycarbonyl) amino]-2-hydroxy-4-phenyl-butanoic acid

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

(2S,3R)-3-[(5-Chloro-1H-indole-2-carbonyl)-amino]-2-hydroxy-4-phenyl-butyric acid

(2S,3R)-3-[(5-Chloro-1H-indole-2-carbonyl)-amino]-2-hydroxy-4-phenyl-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / Me3SiCl / Heating
2: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole, Et3N / CH2Cl2 / 18 h / 23 °C
3: aq. NaOH / methanol / 2 h / 25 °C
View Scheme
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

(2S,3R)-3-[(5-Chloro-1H-indole-2-carbonyl)-amino]-2-hydroxy-4-phenyl-butyric acid methyl ester

(2S,3R)-3-[(5-Chloro-1H-indole-2-carbonyl)-amino]-2-hydroxy-4-phenyl-butyric acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / Me3SiCl / Heating
2: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole, Et3N / CH2Cl2 / 18 h / 23 °C
View Scheme
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

5-Chloro-1H-indole-2-carboxylic acid ((1R,2S)-1-benzyl-2-dimethylcarbamoyl-2-hydroxy-ethyl)-amide

5-Chloro-1H-indole-2-carboxylic acid ((1R,2S)-1-benzyl-2-dimethylcarbamoyl-2-hydroxy-ethyl)-amide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 100 percent / Me3SiCl / Heating
2: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole, Et3N / CH2Cl2 / 18 h / 23 °C
3: aq. NaOH / methanol / 2 h / 25 °C
4: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole, Et3N / dimethylformamide / 18 h / 23 °C
View Scheme
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate
60016-66-2

benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1N NaOH / diethyl ether; H2O
2: 95 percent / DCC, HOBt, Et3N / CH2Cl2; tetrahydrofuran
View Scheme
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
59554-14-2

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

bestatin
58970-76-6

bestatin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1N NaOH / diethyl ether; H2O
2: 95 percent / DCC, HOBt, Et3N / CH2Cl2; tetrahydrofuran
3: H2 / Pd black / H2O; methanol
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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