(2S,3S)-1-bromo-3-<(tert-butoxycarbonyl)amino>-4-phenyl-2-butanol
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
With potassium hydroxide In methanol for 3h; Ambient temperature; | 100% |
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
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 20℃; | 99% |
((S)-1-benzylallyl)carbamic acid tert-butyl ester
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
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% |
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran; ethanol at -15℃; for 2h; Temperature; Inert atmosphere; | 98% |
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 5℃; for 0.5h; | 95% |
(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
Conditions | Yield |
---|---|
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
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
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
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In chloroform for 50h; Heating; | 88% |
With triphenylphosphine; diethylazodicarboxylate | 27% |
With triphenylphosphine; diethylazodicarboxylate In chloroform for 36h; Heating; Yield given; |
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran; isopropyl alcohol at 17℃; for 1.83333h; | 88% |
C22H29NO6S
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at 0℃; for 1h; | 78% |
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
Conditions | Yield |
---|---|
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
A
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
B
(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
In hexane at 5 - 45℃; for 1h; Reagent/catalyst; Temperature; Time; | A 71% B 14% |
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
With caesium carbonate In methanol | 50% |
methylenedimethyl sulfurane
Boc-L-phenylalaninal
A
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
B
(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran at -5℃; for 0.5h; Yield given. Yields of byproduct given; |
((S)-1-benzylallyl)carbamic acid tert-butyl ester
A
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
B
(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
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
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
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
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
With sodium hydroxide In toluene at 20℃; for 2h; | 22.5 mg |
(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
B
(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
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
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
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 |
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
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
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
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
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
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
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
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
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
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
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
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
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
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 |
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
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
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
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-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
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
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 88 percent / aq.Na2CO3 2: 82 percent / MCPBA / CH2Cl2 View Scheme |
4-Bromophenethylamine
(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
Conditions | Yield |
---|---|
In isopropyl alcohol at 50℃; | 96% |
isobutylamine
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
(2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol
Conditions | Yield |
---|---|
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
(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
Conditions | Yield |
---|---|
With isopropyl alcohol at 70℃; | 93% |
piperazine
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
In isopropyl alcohol for 16h; Reflux; regioselective reaction; | 93% |
isobutylamine
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
4-methoxy-phenyl-sulphonyl chloride
tert-butyl (1S,2R)-1-benzyl-2-hydroxy-3-{isobutyl[(4-methoxyphenyl)sulfonyl]amino}propylcarbamate
Conditions | Yield |
---|---|
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
tert-butyl (2S,3S)-4-azido-3-hydroxy-1-phenylbutan-2-ylcarbamate
Conditions | Yield |
---|---|
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
(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 | Yield |
---|---|
With triethylamine In methanol at 80℃; for 24h; | 90% |
(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
methyl (S)-1-(2-(biphenyl-4-ylmethyl)-2-((2S,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutyl)hydrazinyl)-3,3-dioxobutan-2-ylcarbamate
Conditions | Yield |
---|---|
In isopropyl alcohol for 16h; Reflux; | 90% |
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
phenethylamine
(2S,3S)-3-[N-(tert-butyloxycarbonyl)amino]-4-phenyl-1-[(2-phenylethyl)amino]butan-2-ol
Conditions | Yield |
---|---|
In isopropyl alcohol at 50℃; | 88% |
prolylisoleucyclvaline methyl ester hydrochloride
(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
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
In isopropyl alcohol for 16h; Heating; | 86% |
3-bromobenzylamine
(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
Conditions | Yield |
---|---|
In isopropyl alcohol at 50℃; | 86% |
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
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
Conditions | Yield |
---|---|
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
(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
Conditions | Yield |
---|---|
In isopropyl alcohol 1.) 70 deg C, 9 h, 2.) r.t., 16 h; | 84% |
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
With phosphazene base-P4-tert-butyl In tetrahydrofuran at 23℃; for 40h; Inert atmosphere; | 84% |
H-L-Leu-NH2
(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
Conditions | Yield |
---|---|
In isopropyl alcohol Heating; | 83% |
4-Bromobenzylamine
(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
Conditions | Yield |
---|---|
In isopropyl alcohol at 50℃; | 83% |
(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
(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 | Yield |
---|---|
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
benzylamine
(2S,3S)-1-(benzylamino)-3-[N-(tert-butyloxycarbonyl)amino]-4-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
diethyl malonate
(5S,1'S)-carbetoxy-5-<1-<<(1',1-dimethylothoxy)carbonyl>amino>-2-phenylmethyl>dihydrofuran-2(3H)-one
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol at 0 - 25℃; | 82% |
With sodium ethanolate In ethanol at 0 - 25℃; for 18.1666h; |
4-ethoxycarbonylpyrazole
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 1h; Microwave irradiation; | 81.2% |
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 (CAS NO.98760-08-8) is used as atazanavir intermediate.
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