Product Name

  • Name

    (2R,3S)-3-(tert-Butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane

  • EINECS 619-374-7
  • CAS No. 98760-08-8
  • Article Data75
  • CAS DataBase
  • Density 1.118 g/cm3
  • Solubility
  • Melting Point
  • Formula C15H21NO3
  • Boiling Point 398.837 °C at 760 mmHg
  • Molecular Weight 263.337
  • Flash Point 195.01°C
  • Transport Information
  • Appearance white crystalline powder
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 98760-08-8 ((2R,3S)-3-(tert-Butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane)
  • Hazard Symbols
  • Synonyms Carbamicacid, (1-oxiranyl-2-phenylethyl)-, 1,1-dimethylethyl ester, [R-(R*,S*)]-;Carbamic acid, [(1S)-1-(2R)-oxiranyl-2-phenylethyl]-, 1,1-dimethylethyl ester(9CI);tert-Butyl [(1S)-1-[(2R)-oxiranyl]2-phenylethyl]carbamate;
  • PSA 50.86000
  • LogP 2.91210

Synthetic route

(2S,3S)-1-bromo-3-<(tert-butoxycarbonyl)amino>-4-phenyl-2-butanol
136630-87-0

(2S,3S)-1-bromo-3-<(tert-butoxycarbonyl)amino>-4-phenyl-2-butanol

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
With potassium hydroxide In methanol for 3h; Ambient temperature;100%
Acetic acid (1R,2S)-1-bromomethyl-2-tert-butoxycarbonylamino-3-phenyl-propyl ester
200616-28-0

Acetic acid (1R,2S)-1-bromomethyl-2-tert-butoxycarbonylamino-3-phenyl-propyl ester

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
With potassium carbonate In methanol at 20℃;99%
((S)-1-benzylallyl)carbamic acid tert-butyl ester
103127-52-2, 107202-43-7

((S)-1-benzylallyl)carbamic acid tert-butyl ester

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 2h; Concentration;98.7%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 1h; Concentration;97.8%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane Epoxidation;82%
(1S,2S)-(1-benzyl-3-chloro-2-acetyloxypropyl)carbamate tert-butyl ester

(1S,2S)-(1-benzyl-3-chloro-2-acetyloxypropyl)carbamate tert-butyl ester

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran; ethanol at -15℃; for 2h; Temperature; Inert atmosphere;98%
tert-butyl (4S,5R)-4-benzyl-5-(chloromethyl)-2-oxooxazolidine-3-carboxylate

tert-butyl (4S,5R)-4-benzyl-5-(chloromethyl)-2-oxooxazolidine-3-carboxylate

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 5℃; for 0.5h;95%
(2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane
162536-40-5

(2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
With sodium hydroxide In water; isopropyl alcohol at 4℃; for 1 - 2.5h;93.4%
With sodium hydroxide In water; acetone at 25℃; for 3h;93%
With sodium hydroxide In water; isopropyl alcohol at 0℃; for 4h; Product distribution / selectivity;93%
(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-[(methylsulfonyl)oxy]-4-phenylbutyl acetate
259752-50-6

(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-[(methylsulfonyl)oxy]-4-phenylbutyl acetate

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; methanol at 25℃; for 20h;90%
With potassium carbonate In tetrahydrofuran; methanol at 20 - 30℃; for 15h; Inert atmosphere;90%
((1S,2R)-1-benzyl-2,3-dihydroxypropyl)carbamic acid tert-butyl ester
99113-35-6

((1S,2R)-1-benzyl-2,3-dihydroxypropyl)carbamic acid tert-butyl ester

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In chloroform for 50h; Heating;88%
With triphenylphosphine; diethylazodicarboxylate27%
With triphenylphosphine; diethylazodicarboxylate In chloroform for 36h; Heating; Yield given;
C16H25NO6S

C16H25NO6S

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran; isopropyl alcohol at 17℃; for 1.83333h;88%
C22H29NO6S
170359-21-4

C22H29NO6S

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
With potassium hydroxide In methanol at 0℃; for 1h;78%
tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
165727-45-7

tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
With sodium hydroxide In methanol; ethanol at 0 - 20℃; for 4.5h; Time;74%
Multi-step reaction with 3 steps
1: thionyl chloride / tert-butyl methyl ether / 8 h / 10 - 55 °C
2: triethylamine; dmap / tert-butyl methyl ether / 8 h / 10 - 20 °C
3: potassium hydroxide / ethanol / 0.5 h / 5 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / toluene / 2 h / 35 °C / Inert atmosphere
2: 18-crown-6 ether / toluene / 3 h / 70 °C
3: potassium hydroxide / tetrahydrofuran; ethanol / 2 h / -15 °C / Inert atmosphere
View Scheme
1(R,S)-<1'-(S)-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>oxirane
220871-52-3

1(R,S)-<1'-(S)-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>oxirane

A

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

B

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester
98760-08-8, 98818-34-9, 98818-35-0, 103127-56-6, 98737-29-2

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
In hexane at 5 - 45℃; for 1h; Reagent/catalyst; Temperature; Time;A 71%
B 14%
(4S,5R)-4-Benzyl-2-oxo-5-(toluene-4-sulfonyloxymethyl)-oxazolidine-3-carboxylic acid tert-butyl ester

(4S,5R)-4-Benzyl-2-oxo-5-(toluene-4-sulfonyloxymethyl)-oxazolidine-3-carboxylic acid tert-butyl ester

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
With caesium carbonate In methanol50%
methylenedimethyl sulfurane
6814-64-8, 40651-06-7

methylenedimethyl sulfurane

Boc-L-phenylalaninal
72155-45-4

Boc-L-phenylalaninal

A

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

B

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester
98760-08-8, 98818-34-9, 98818-35-0, 103127-56-6, 98737-29-2

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
In tetrahydrofuran at -5℃; for 0.5h; Yield given. Yields of byproduct given;
((S)-1-benzylallyl)carbamic acid tert-butyl ester
103127-52-2, 107202-43-7

((S)-1-benzylallyl)carbamic acid tert-butyl ester

A

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

B

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester
98760-08-8, 98818-34-9, 98818-35-0, 103127-56-6, 98737-29-2

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 20h; Product distribution; Heating; various temperatures and concentrations of MCPBA;
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; Yield given. Yields of byproduct given;
With 3-chloro-benzenecarboperoxoic acid In dichloromethane Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With 3-chloro-benzenecarboperoxoic acid In dichloromethane optical yield given as %de;
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate; Oxone / water; acetone; ethyl acetate / 17 h
2: hexane / 1 h / 5 - 45 °C
View Scheme
methanesulfonic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenyl-propyl ester
437713-03-6

methanesulfonic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenyl-propyl ester

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; sodium methylate In tetrahydrofuran Hydrolysis; cyclization;
Multi-step reaction with 2 steps
1: ammonium fluoride; acetic acid / methanol / 11 h / 20 °C / Large scale
2: potassium tert-butylate / isopropyl alcohol; tetrahydrofuran / 1.83 h / 17 °C
View Scheme
N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-methane sulfonyloxybutane
233662-06-1

N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-methane sulfonyloxybutane

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
With sodium hydroxide In toluene at 20℃; for 2h;22.5 mg
(S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate
102123-74-0

(S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate

A

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

B

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester
98760-08-8, 98818-34-9, 98818-35-0, 103127-56-6, 98737-29-2

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: (S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate With formic acid; triethylamine; (pentamethylcyclopentadienyl)RhCl[(S,S)-Tsdpen] In isopropyl alcohol at 25℃;
Stage #2: With sodium hydroxide In isopropyl alcohol at 0℃;
Stage #3: With water
Stage #1: (S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate With formic acid; triethylamine; (C5Me5)(Cl)Rh((1R,2R)-N-p-tosyl-1,2-diphenylethylenediamine) In isopropyl alcohol at 25℃;
Stage #2: With sodium hydroxide In isopropyl alcohol at 0℃;
Stage #3: With water
(2R,3S)-3-Amino-4-phenyl-butane-1,2-diol
109389-10-8

(2R,3S)-3-Amino-4-phenyl-butane-1,2-diol

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Et3N / methanol / 20 °C
2: p-TsOH; pyridine / CH2Cl2 / 20 °C
3: CH2Cl2 / 20 °C
4: 99 percent / K2CO3 / methanol / 20 °C
View Scheme
[(S)-1-((S)-2-Methoxy-2-methyl-[1,3]dioxolan-4-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

[(S)-1-((S)-2-Methoxy-2-methyl-[1,3]dioxolan-4-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CH2Cl2 / 20 °C
2: 99 percent / K2CO3 / methanol / 20 °C
View Scheme
(3S)-3-(N,N-dibenzyl)amino-1-methylsulfinyl-2-oxo-4-phenylbutane
184537-69-7

(3S)-3-(N,N-dibenzyl)amino-1-methylsulfinyl-2-oxo-4-phenylbutane

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: aq. HCl / dimethylsulfoxide / 15 h / 20 °C
2: 56.2 mg / NaBH4 / aq. ethanol / 0.83 h / 0 °C
3: H2 / Pd/C / methanol / 20 °C
4: Et3N / methanol / 20 °C
5: p-TsOH; pyridine / CH2Cl2 / 20 °C
6: CH2Cl2 / 20 °C
7: 99 percent / K2CO3 / methanol / 20 °C
View Scheme
(3S)-3-(N,N-dibenzyl)amino-1-hydroxy-1-methylthio-2-oxo-4-phenylbutane
189562-37-6

(3S)-3-(N,N-dibenzyl)amino-1-hydroxy-1-methylthio-2-oxo-4-phenylbutane

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 56.2 mg / NaBH4 / aq. ethanol / 0.83 h / 0 °C
2: H2 / Pd/C / methanol / 20 °C
3: Et3N / methanol / 20 °C
4: p-TsOH; pyridine / CH2Cl2 / 20 °C
5: CH2Cl2 / 20 °C
6: 99 percent / K2CO3 / methanol / 20 °C
View Scheme
N,N-dibenzyl-L-phenylalanine benzyl ester
111138-83-1

N,N-dibenzyl-L-phenylalanine benzyl ester

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: NaNH2 / tetrahydrofuran / 0 °C
1.2: aq. citric acid
2.1: aq. HCl / dimethylsulfoxide / 15 h / 20 °C
3.1: 56.2 mg / NaBH4 / aq. ethanol / 0.83 h / 0 °C
4.1: H2 / Pd/C / methanol / 20 °C
5.1: Et3N / methanol / 20 °C
6.1: p-TsOH; pyridine / CH2Cl2 / 20 °C
7.1: CH2Cl2 / 20 °C
8.1: 99 percent / K2CO3 / methanol / 20 °C
View Scheme
(2R,3S)-3-dibenzylamino-5-phenylbutane-1,2-diol
200616-26-8

(2R,3S)-3-dibenzylamino-5-phenylbutane-1,2-diol

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: H2 / Pd/C / methanol / 20 °C
2: Et3N / methanol / 20 °C
3: p-TsOH; pyridine / CH2Cl2 / 20 °C
4: CH2Cl2 / 20 °C
5: 99 percent / K2CO3 / methanol / 20 °C
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 85 percent / aq. NaOH; Na2CO3 / dioxane / 8 h / 20 °C
2.1: 97 percent / K2CO3 / dimethylformamide / 10 h / 20 °C
3.1: NaBH4 / methanol / 0.5 h / 0 °C
3.2: 85 percent / LiCl / methanol / 0 - 20 °C
4.1: Et3N / toluene / 0 - 20 °C
5.1: 22.5 mg / aq. NaOH / toluene / 2 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: CH2Cl2 / 3.5 h / 23 °C
2: 1.) O3, 2.) NaBH4 / 1.) EtOH, -78 deg C, 45 min, 2.) EtOH, 23 deg C, 1 h
3: 88 percent / PPh3, DEAD / CHCl3 / 50 h / Heating
View Scheme
Multi-step reaction with 4 steps
2: 95 percent / Et3N, DMAP / 20 h / Ambient temperature
3: LiAlH4 / diethyl ether / 4 h / Heating
4: Ph3P, DEAD / CHCl3 / 36 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: 1.) CAN
2: 95 percent / Et3N, DMAP / 20 h / Ambient temperature
3: LiAlH4 / diethyl ether / 4 h / Heating
4: Ph3P, DEAD / CHCl3 / 36 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: sodium hydrogencarbonate / isopropyl alcohol; water / 48 h / 20 °C
2: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tert-butyl alcohol / 24 h / 20 °C
3: triphenylphosphine; diethylazodicarboxylate
View Scheme
(2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid
105181-72-4

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

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 97 percent / K2CO3 / dimethylformamide / 10 h / 20 °C
2.1: NaBH4 / methanol / 0.5 h / 0 °C
2.2: 85 percent / LiCl / methanol / 0 - 20 °C
3.1: Et3N / toluene / 0 - 20 °C
4.1: 22.5 mg / aq. NaOH / toluene / 2 h / 20 °C
View Scheme
(2RS,3S)-N-(tert-butoxycarbonyl)-3-amino-2-trimethylsilyloxy-4-phenylbutanenitrile

(2RS,3S)-N-(tert-butoxycarbonyl)-3-amino-2-trimethylsilyloxy-4-phenylbutanenitrile

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 3.47 g / aq. HCl / 48 h / 60 °C
2.1: 85 percent / aq. NaOH; Na2CO3 / dioxane / 8 h / 20 °C
3.1: 97 percent / K2CO3 / dimethylformamide / 10 h / 20 °C
4.1: NaBH4 / methanol / 0.5 h / 0 °C
4.2: 85 percent / LiCl / methanol / 0 - 20 °C
5.1: Et3N / toluene / 0 - 20 °C
6.1: 22.5 mg / aq. NaOH / toluene / 2 h / 20 °C
View Scheme
(2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester
116565-10-7

(2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: NaBH4 / methanol / 0.5 h / 0 °C
1.2: 85 percent / LiCl / methanol / 0 - 20 °C
2.1: Et3N / toluene / 0 - 20 °C
3.1: 22.5 mg / aq. NaOH / toluene / 2 h / 20 °C
View Scheme
(2R,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid hydrochloride

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

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 85 percent / aq. NaOH; Na2CO3 / dioxane / 8 h / 20 °C
2.1: 97 percent / K2CO3 / dimethylformamide / 10 h / 20 °C
3.1: NaBH4 / methanol / 0.5 h / 0 °C
3.2: 85 percent / LiCl / methanol / 0 - 20 °C
4.1: Et3N / toluene / 0 - 20 °C
5.1: 22.5 mg / aq. NaOH / toluene / 2 h / 20 °C
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

pentacarbonyl<1-<<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl>oxy>-(E)-3-phenyl-2-propenylidene>chromium

pentacarbonyl<1-<<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl>oxy>-(E)-3-phenyl-2-propenylidene>chromium

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88 percent / aq.Na2CO3
2: 82 percent / MCPBA / CH2Cl2
View Scheme
4-Bromophenethylamine
73918-56-6

4-Bromophenethylamine

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

(2S,3S)-1-{[2-(4-bromophenyl)ethyl]amino}-3-[N-(tert-butyloxycarbonyl)amino]-4-phenylbutan-2-ol
866227-26-1

(2S,3S)-1-{[2-(4-bromophenyl)ethyl]amino}-3-[N-(tert-butyloxycarbonyl)amino]-4-phenylbutan-2-ol

Conditions
ConditionsYield
In isopropyl alcohol at 50℃;96%
isobutylamine
78-81-9

isobutylamine

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

(2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol
160232-08-6

(2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol

Conditions
ConditionsYield
In isopropyl alcohol at 20 - 30℃; Solvent;94.67%
In isopropyl alcohol at 80℃; for 2.5h;93%
In isopropyl alcohol at 80℃; for 2.5h;
2-amino-N-(1,1-dimethylethyl)benzamide
1203-89-0

2-amino-N-(1,1-dimethylethyl)benzamide

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

[(1S,2S)-1-Benzyl-3-(2-tert-butylcarbamoyl-phenylamino)-2-hydroxy-propyl]-carbamic acid tert-butyl ester
152303-48-5

[(1S,2S)-1-Benzyl-3-(2-tert-butylcarbamoyl-phenylamino)-2-hydroxy-propyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With isopropyl alcohol at 70℃;93%
piperazine
110-85-0

piperazine

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

di-tert-butyl ((2S,2′S,3R,3′R)-piperazine-1,4-diylbis(3-hydroxy-1-phenylbutane-4,2-diyl))dicarbamate

di-tert-butyl ((2S,2′S,3R,3′R)-piperazine-1,4-diylbis(3-hydroxy-1-phenylbutane-4,2-diyl))dicarbamate

Conditions
ConditionsYield
In isopropyl alcohol for 16h; Reflux; regioselective reaction;93%
isobutylamine
78-81-9

isobutylamine

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

4-methoxy-phenyl-sulphonyl chloride
98-68-0

4-methoxy-phenyl-sulphonyl chloride

tert-butyl (1S,2R)-1-benzyl-2-hydroxy-3-{isobutyl[(4-methoxyphenyl)sulfonyl]amino}propylcarbamate
159006-03-8

tert-butyl (1S,2R)-1-benzyl-2-hydroxy-3-{isobutyl[(4-methoxyphenyl)sulfonyl]amino}propylcarbamate

Conditions
ConditionsYield
Stage #1: isobutylamine; (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane In isopropyl alcohol at 80℃; for 2h;
Stage #2: 4-methoxy-phenyl-sulphonyl chloride With triethylamine In dichloromethane at 25℃; for 1h;
92%
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

tert-butyl (2S,3S)-4-azido-3-hydroxy-1-phenylbutan-2-ylcarbamate
1385766-21-1

tert-butyl (2S,3S)-4-azido-3-hydroxy-1-phenylbutan-2-ylcarbamate

Conditions
ConditionsYield
With sodium azide; ammonium chloride In methanol Reflux;90.3%
With sodium azide; ammonium chloride In ethanol; water at 85℃; for 16h;
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

(S)-2-[((R)-5,5-Dimethyl-thiazolidine-4-carbonyl)-amino]-3-methyl-butyric acid methyl ester

(S)-2-[((R)-5,5-Dimethyl-thiazolidine-4-carbonyl)-amino]-3-methyl-butyric acid methyl ester

(S)-2-{[(R)-3-((2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-5,5-dimethyl-thiazolidine-4-carbonyl]-amino}-3-methyl-butyric acid methyl ester
359690-94-1

(S)-2-{[(R)-3-((2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-5,5-dimethyl-thiazolidine-4-carbonyl]-amino}-3-methyl-butyric acid methyl ester

Conditions
ConditionsYield
With triethylamine In methanol at 80℃; for 24h;90%
(S)-methyl 1-(2-(biphenyl-4-ylmethyl)hydrazinyl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate
1313358-60-9

(S)-methyl 1-(2-(biphenyl-4-ylmethyl)hydrazinyl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

methyl (S)-1-(2-(biphenyl-4-ylmethyl)-2-((2S,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutyl)hydrazinyl)-3,3-dioxobutan-2-ylcarbamate
1313358-61-0

methyl (S)-1-(2-(biphenyl-4-ylmethyl)-2-((2S,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutyl)hydrazinyl)-3,3-dioxobutan-2-ylcarbamate

Conditions
ConditionsYield
In isopropyl alcohol for 16h; Reflux;90%
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

phenethylamine
64-04-0

phenethylamine

(2S,3S)-3-[N-(tert-butyloxycarbonyl)amino]-4-phenyl-1-[(2-phenylethyl)amino]butan-2-ol
866227-22-7

(2S,3S)-3-[N-(tert-butyloxycarbonyl)amino]-4-phenyl-1-[(2-phenylethyl)amino]butan-2-ol

Conditions
ConditionsYield
In isopropyl alcohol at 50℃;88%
prolylisoleucyclvaline methyl ester hydrochloride
132234-31-2

prolylisoleucyclvaline methyl ester hydrochloride

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

(2S,3S)-3--2-hydroxy-4-phenyl-1-(N-prolylisoleucylvaline methyl ester)butane
132259-52-0

(2S,3S)-3--2-hydroxy-4-phenyl-1-(N-prolylisoleucylvaline methyl ester)butane

Conditions
ConditionsYield
With triethylamine In methanol Heating;87%
With triethylamine In di-isopropyl ether for 24h; Heating;
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

1-([1,1'-biphenyl]-4-ylmethyl)-2-Boc-hydrazine
162739-87-9

1-([1,1'-biphenyl]-4-ylmethyl)-2-Boc-hydrazine

1-(4-Biphenylyl)-5(S)-2,5-di[(tert-butoxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane
191594-83-9

1-(4-Biphenylyl)-5(S)-2,5-di[(tert-butoxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane

Conditions
ConditionsYield
In isopropyl alcohol for 16h; Heating;86%
3-bromobenzylamine
10269-01-9

3-bromobenzylamine

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

(2S,3S)-1-[(3-bromobenzyl)amino]-3-[N-(tert-butyloxycarbonyl)amino]-4-phenylbutan-2-ol
866227-25-0

(2S,3S)-1-[(3-bromobenzyl)amino]-3-[N-(tert-butyloxycarbonyl)amino]-4-phenylbutan-2-ol

Conditions
ConditionsYield
In isopropyl alcohol at 50℃;86%
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine
198904-85-7

N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine

1-[4-(pyridine-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane
198904-86-8

1-[4-(pyridine-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane

Conditions
ConditionsYield
In isopropyl alcohol for 24h; Inert atmosphere; Reflux; Large scale;85.4%
In isopropyl alcohol Heating / reflux;75%
In isopropyl alcohol for 16h; Heating;69%
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide
128019-40-9, 149510-73-6, 136465-81-1

(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide

[(1S,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propyl]-carbamic acid tert-butyl ester
142580-65-2

[(1S,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
In isopropyl alcohol 1.) 70 deg C, 9 h, 2.) r.t., 16 h;84%
3,4-dichloro-N-isopropoxybenzenesulfonamide

3,4-dichloro-N-isopropoxybenzenesulfonamide

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

tert-butyl ((1S,2S)-3-((3,4-dichloro-N-isopropoxyphenyl)sulfonamido)-2-hydroxy-1-phenylpropyl)carbamate

tert-butyl ((1S,2S)-3-((3,4-dichloro-N-isopropoxyphenyl)sulfonamido)-2-hydroxy-1-phenylpropyl)carbamate

Conditions
ConditionsYield
With phosphazene base-P4-tert-butyl In tetrahydrofuran at 23℃; for 40h; Inert atmosphere;84%
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

(2S,5S,6S)-3-aza-6-[(tert-butyloxycarbonyl)amino]-2-isobutyl-5-hydroxy-7-phenylheptanoyl amide
500767-13-5

(2S,5S,6S)-3-aza-6-[(tert-butyloxycarbonyl)amino]-2-isobutyl-5-hydroxy-7-phenylheptanoyl amide

Conditions
ConditionsYield
In isopropyl alcohol Heating;83%
4-Bromobenzylamine
3959-07-7

4-Bromobenzylamine

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

(2S,3S)-1-[(4-bromobenzyl)amino]-3-[N-(tert-butyloxycarbonyl)amino]-4-phenylbutan-2-ol
866227-24-9

(2S,3S)-1-[(4-bromobenzyl)amino]-3-[N-(tert-butyloxycarbonyl)amino]-4-phenylbutan-2-ol

Conditions
ConditionsYield
In isopropyl alcohol at 50℃;83%
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

(2R,4R)-4-Benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester
147240-29-7

(2R,4R)-4-Benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester

(2R,4S)-4-Benzyl-4-((2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester
160978-16-5

(2R,4S)-4-Benzyl-4-((2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester

Conditions
ConditionsYield
With diethylaluminium chloride; potassium hexamethylsilazane In tetrahydrofuran at -78℃;82%
With diethylaluminium chloride; potassium hexamethylsilazane 1.) THF, toluene, -78 deg C, 10 min, 2.) THF, toluene, heptane, -74 deg C, 10 min; Yield given. Multistep reaction;
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

benzylamine
100-46-9

benzylamine

(2S,3S)-1-(benzylamino)-3-[N-(tert-butyloxycarbonyl)amino]-4-phenylbutan-2-ol
143577-00-8

(2S,3S)-1-(benzylamino)-3-[N-(tert-butyloxycarbonyl)amino]-4-phenylbutan-2-ol

Conditions
ConditionsYield
In isopropyl alcohol at 50℃;82%
With pyridine In isopropyl alcohol for 16h; Reflux;47%
In isopropyl alcohol for 16h; Heating;
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

diethyl malonate
105-53-3

diethyl malonate

(5S,1'S)-carbetoxy-5-<1-<<(1',1-dimethylothoxy)carbonyl>amino>-2-phenylmethyl>dihydrofuran-2(3H)-one
193338-94-2

(5S,1'S)-carbetoxy-5-<1-<<(1',1-dimethylothoxy)carbonyl>amino>-2-phenylmethyl>dihydrofuran-2(3H)-one

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 0 - 25℃;82%
With sodium ethanolate In ethanol at 0 - 25℃; for 18.1666h;
4-ethoxycarbonylpyrazole
37622-90-5

4-ethoxycarbonylpyrazole

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

C21H29N3O5

C21H29N3O5

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 1h; Microwave irradiation;81.2%

(2R,3S)-3-(tert-Butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane Chemical Properties

IUPAC Name: tert-Butyl N-[(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl]carbamate
Synonyms of (2R,3S)-3-(tert-Butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane (CAS NO.98760-08-8): (2R,3S)-3-(N-Boc-amino)-1-oxirane-4-phenylbutane
CAS NO: 98760-08-8
Molecular Formula: C15H21NO3
Molecular Weight: 263.34
Molecular Structure:
H bond acceptors: 4
H bond donors: 1
Freely Rotating Bonds: 6
Polar Surface Area: 50.86 Å2
Index of Refraction: 1.533
Molar Refractivity: 73.048 cm3
Molar Volume: 235.468 cm3
Surface Tension: 42.455 dyne/cm
Density: 1.118 g/cm3
Flash Point: 195.01 °C
Enthalpy of Vaporization: 64.947 kJ/mol
Boiling Point: 398.837 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C
Appearance: White Crystalline Powder
SMILES: O=C(OC(C)(C)C)N[C@H]([C@H]1OC1)Cc2ccccc2
InChI: InChI=1/C15H21NO3/c1-15(2,3)19-14(17)16-12(13-10-18-13)9-11-7-5-4-6-8-11/h4-8,12-13H,9-10H2,1-3H3,(H,16,17)/t12-,13-/m0/s1
InChIKey: NVPOUMXZERMIJK-STQMWFEEBJ
Std. InChI: InChI=1S/C15H21NO3/c1-15(2,3)19-14(17)16-12(13-10-18-13)9-11-7-5-4-6-8-11/h4-8,12-13H,9-10H2,1-3H3,(H,16,17)/t12-,13-/m0/s1
Std. InChIKey: NVPOUMXZERMIJK-STQMWFEESA-N
Product Categories of (2R,3S)-3-(tert-Butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane (CAS NO.98760-08-8): Chiral Amino Epoxides;chiral;Aromatics Compounds;Aromatics;Chiral Reagents;Heterocycles

(2R,3S)-3-(tert-Butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane Uses

 (2R,3S)-3-(tert-Butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane (CAS NO.98760-08-8) is used as atazanavir intermediate.

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