(2S,3R)-3-Amino-2-hydroxy-4-phenyl-butyric acid isopropyl ester
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; ion exchange resin (H+) 1.) 4 h, 100 deg C; | 85% |
(2S,3R)-2-hydroxy-4-phenyl-3-(tosylamino)butanoic acid
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
With Na-naphthalide In 1,2-dimethoxyethane at -78℃; for 0.5h; | 82% |
(2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenyl-butanoic acid
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
With hydrogen; palladium |
methyl (4R,5S)-2-oxo-4-phenylmethyl-1,3-oxazolidine-5-carboxylate
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
With lithium hydroxide In methanol; water |
methyl (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoate
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride |
(2S,3R)-2-O-benzyl-4-phenyl-3-[(9-phenyl-9-fluorenyl)-amino]-phenylbutanoic acid
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol at 70℃; for 12h; |
(2S,3R)-3-azido-2-hydroxy-4-phenylbutanoic acid
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water for 8h; Heating; |
ethyl (2R,3S)-4-phenyl-2,3-oxiranebutanoate
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: 2N LiOH / methanol; H2O View Scheme |
N-<(benzyloxy)carbonyl>-(2R)-amino-1-phenylbut-3-ene
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 82 percent / Na / NH3 3: 2N LiOH / methanol; H2O View Scheme |
Z-D-phenylalanine ethyl ester
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
With chloro-trimethyl-silane Heating; | 100% |
di-tert-butyl dicarbonate
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
(2S,3R)-3-[(tert-butoxycarbonyl) amino]-2-hydroxy-4-phenyl-butanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; for 1h; | 100% |
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
benzyl chloroformate
(2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenyl-butanoic acid
Conditions | Yield |
---|---|
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
(2S,3R)-3-[(tert-butoxycarbonyl) amino]-2-hydroxy-4-phenyl-butanoic acid
(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate
Conditions | Yield |
---|---|
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
bestatin
Conditions | Yield |
---|---|
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 |
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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