98760-08-8

Basic information

• Product Name: (2R,3S)-3-(tert-Butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane
• Synonyms: (2R, 3S)-1,2-EPOXY-3-N-(TERT-BUTOXYCARBONYL)AMINO-4-PHENYLBUTANE;(2r,3s)-3-(n-boc-amino)-1-oxirane-4-phenylbutane;(2R,3S)-3-(tert-Butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane;[1(S)-BENZYL-2(R),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER;THREO-N-BOC-L-PHENYLALANINE EPOXIDE;TERT-BUTYL (1S)-1-[(2R)-OXIRAN-2-YL]-2-PHENYLETHYLCARBAMATE;Tert-Butyl[(1S)-1-(2R)-Oxiranyl-2-Phenylethyl]carbamate;Carbamic acid,[(1S)-1-(2R)-oxiranyl-2-phenylethyl]-,1,1-dimethylethyl ester
• CAS NO: 98760-08-8
• Molecular Formula: C₁₅H₂₁NO₃
• Molecular Weight: 263.33
• EINECS: 2017-001-1
• Product Categories: Chiral Amino Epoxides;chiral;Aromatics Compounds;Aromatics;Chiral Reagents;Heterocycles
• Mol File: 98760-08-8.mol
• Article Data: 75

Chemical Properties

• Boiling Point: 398.837 °C at 760 mmHg
• Flash Point: 195.01°C
• Appearance: white crystalline powder
• Density: 1.118 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 12.19±0.46(Predicted)
• CAS DataBase Reference: (2R,3S)-3-(tert-Butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-3-(tert-Butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane(98760-08-8)
• EPA Substance Registry System: (2R,3S)-3-(tert-Butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane(98760-08-8)

Safety Data

• Hazardous Substances Data: 98760-08-8(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Powder

Uses

Different sources of media describe the Uses of 98760-08-8 differently. You can refer to the following data:
1. Atazanavir intermediate. Enantiomer R
2. Atazanavir, Amprenavir Intermediate

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

Synthetic route

(2S,3S)-1-bromo-3-<(tert-butoxycarbonyl)amino>-4-phenyl-2-butanol (136630-87-0) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

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 (200616-28-0) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

Conditions	Yield
With potassium carbonate In methanol at 20℃;	99%

((S)-1-benzylallyl)carbamic acid tert-butyl ester (103127-52-2, 107202-43-7) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

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%

(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)

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

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 (162536-40-5) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

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 (259752-50-6) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

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 (99113-35-6) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

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;

C16H25NO6S → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; isopropyl alcohol at 17℃; for 1.83333h;	88%

C22H29NO6S (170359-21-4) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

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 (165727-45-7) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

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 (220871-52-3) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) + (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester (98760-08-8, 98818-34-9, 98818-35-0, 103127-56-6, 98737-29-2)

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

Conditions	Yield
With caesium carbonate In methanol	50%

methylenedimethyl sulfurane (6814-64-8, 40651-06-7) + Boc-L-phenylalaninal (72155-45-4) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) + (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester (98760-08-8, 98818-34-9, 98818-35-0, 103127-56-6, 98737-29-2)

Conditions	Yield
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) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) + (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester (98760-08-8, 98818-34-9, 98818-35-0, 103127-56-6, 98737-29-2)

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 (437713-03-6) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

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 (233662-06-1) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

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 (102123-74-0) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) + (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester (98760-08-8, 98818-34-9, 98818-35-0, 103127-56-6, 98737-29-2)

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 (109389-10-8) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

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

[(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)

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 (184537-69-7) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

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 (189562-37-6) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

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 (111138-83-1) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

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 (200616-26-8) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

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 (24424-99-5) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

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 (105181-72-4) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

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

(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)

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 (116565-10-7) → (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8)

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

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 (24424-99-5) + 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)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / aq.Na2CO3 2: 82 percent / MCPBA / CH2Cl2 View Scheme

4-Bromophenethylamine (73918-56-6) + (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) → (2S,3S)-1-{[2-(4-bromophenyl)ethyl]amino}-3-[N-(tert-butyloxycarbonyl)amino]-4-phenylbutan-2-ol (866227-26-1)

Conditions	Yield
In isopropyl alcohol at 50℃;	96%

isobutylamine (78-81-9) + (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) → (2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol (160232-08-6)

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 (1203-89-0) + (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) → [(1S,2S)-1-Benzyl-3-(2-tert-butylcarbamoyl-phenylamino)-2-hydroxy-propyl]-carbamic acid tert-butyl ester (152303-48-5)

Conditions	Yield
With isopropyl alcohol at 70℃;	93%

piperazine (110-85-0) + (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) → di-tert-butyl ((2S,2′S,3R,3′R)-piperazine-1,4-diylbis(3-hydroxy-1-phenylbutane-4,2-diyl))dicarbamate

Conditions	Yield
In isopropyl alcohol for 16h; Reflux; regioselective reaction;	93%

isobutylamine (78-81-9) + (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) + 4-methoxy-phenyl-sulphonyl chloride (98-68-0) → tert-butyl (1S,2R)-1-benzyl-2-hydroxy-3-{isobutyl[(4-methoxyphenyl)sulfonyl]amino}propylcarbamate (159006-03-8)

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 (98760-08-8) → tert-butyl (2S,3S)-4-azido-3-hydroxy-1-phenylbutan-2-ylcarbamate (1385766-21-1)

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 (98760-08-8) + (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)

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 (1313358-60-9) + (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) → 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)

Conditions	Yield
In isopropyl alcohol for 16h; Reflux;	90%

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) + phenethylamine (64-04-0) → (2S,3S)-3-[N-(tert-butyloxycarbonyl)amino]-4-phenyl-1-[(2-phenylethyl)amino]butan-2-ol (866227-22-7)

Conditions	Yield
In isopropyl alcohol at 50℃;	88%

prolylisoleucyclvaline methyl ester hydrochloride (132234-31-2) + (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) → (2S,3S)-3--2-hydroxy-4-phenyl-1-(N-prolylisoleucylvaline methyl ester)butane (132259-52-0)

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 (98760-08-8) + 1-([1,1'-biphenyl]-4-ylmethyl)-2-Boc-hydrazine (162739-87-9) → 1-(4-Biphenylyl)-5(S)-2,5-di[(tert-butoxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane (191594-83-9)

Conditions	Yield
In isopropyl alcohol for 16h; Heating;	86%

3-bromobenzylamine (10269-01-9) + (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) → (2S,3S)-1-[(3-bromobenzyl)amino]-3-[N-(tert-butyloxycarbonyl)amino]-4-phenylbutan-2-ol (866227-25-0)

Conditions	Yield
In isopropyl alcohol at 50℃;	86%

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) + N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine (198904-85-7) → 1-[4-(pyridine-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane (198904-86-8)

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 (98760-08-8) + (3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide (128019-40-9, 149510-73-6, 136465-81-1) → [(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)

Conditions	Yield
In isopropyl alcohol 1.) 70 deg C, 9 h, 2.) r.t., 16 h;	84%

3,4-dichloro-N-isopropoxybenzenesulfonamide + (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) → tert-butyl ((1S,2S)-3-((3,4-dichloro-N-isopropoxyphenyl)sulfonamido)-2-hydroxy-1-phenylpropyl)carbamate

Conditions	Yield
With phosphazene base-P4-tert-butyl In tetrahydrofuran at 23℃; for 40h; Inert atmosphere;	84%

H-L-Leu-NH2 (687-51-4, 13079-20-4, 13366-40-0, 15893-47-7) + (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) → (2S,5S,6S)-3-aza-6-[(tert-butyloxycarbonyl)amino]-2-isobutyl-5-hydroxy-7-phenylheptanoyl amide (500767-13-5)

Conditions	Yield
In isopropyl alcohol Heating;	83%

4-Bromobenzylamine (3959-07-7) + (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) → (2S,3S)-1-[(4-bromobenzyl)amino]-3-[N-(tert-butyloxycarbonyl)amino]-4-phenylbutan-2-ol (866227-24-9)

Conditions	Yield
In isopropyl alcohol at 50℃;	83%

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) + (2R,4R)-4-Benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester (147240-29-7) → (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)

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 (98760-08-8) + benzylamine (100-46-9) → (2S,3S)-1-(benzylamino)-3-[N-(tert-butyloxycarbonyl)amino]-4-phenylbutan-2-ol (143577-00-8)

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 (98760-08-8) + diethyl malonate (105-53-3) → (5S,1'S)-carbetoxy-5-<1-<<(1',1-dimethylothoxy)carbonyl>amino>-2-phenylmethyl>dihydrofuran-2(3H)-one (193338-94-2)

Conditions	Yield
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) + (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) → C21H29N3O5

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

Upstream product

• 6814-64-8 methylenedimethyl sulfurane 
• 72155-45-4 Boc-L-phenylalaninal 
• 103127-52-2 ((S)-1-benzylallyl)carbamic acid tert-butyl ester 
• 165727-45-7 tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate 
• 102123-74-0 (S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate 
• 67-63-0 isopropyl alcohol 
• 77-92-9 citric acid 
• 473916-42-6 (S)-tert-butyl 2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)aziridine-1-carboxylate 
• 473916-49-3 (2R,3S)-1,2-O-isopropylidene-3-(t-butoxycarbonyl)amino-4-phenybutane-1,2-diol 
• 99113-35-6 ((1S,2R)-1-benzyl-2,3-dihydroxypropyl)carbamic acid tert-butyl ester 
• 184537-67-5 1,1-dimethylethyl N-[(1S)-3-(methylsulfinyl)-2-oxo-1-(phenylmethyl)propyl]carbamate 
• 126410-30-8 (S)-1-phenylbut-3-en-2-amine 
• 756462-76-7 (R)-1-benzyl-prop-2-enylamine 
• 220871-52-3 1(R,S)-<1'-(S)-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>oxirane 

Downstream Products

• 161852-52-4 N'-((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-N'-(4-hydroxy-benzyl)-hydrazinecarboxylic acid tert-butyl ester 
• 251105-80-3 N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride 
• 252873-22-6 tert-butyl (1S,2R)-1-benzyl-3-[(cyclohexyloxy)amino]-2-hydroxypropylcarbamate 
• 184357-17-3 1,1-dimethylethyl [(1S,2R)-3-[(cyclohexylmethyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-carbamate 
• 228850-43-9 [(1S,2S)-1-Benzyl-3-((2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butylsulfanyl)-2-hydroxy-propyl]-carbamic acid tert-butyl ester 
• 137281-40-4 (-)-tert-butyl ((2S,3S)-3-hydroxy-1-phenylhept-6-en-2-yl)carbamate 
• 190508-37-3 (2S,4R)-1-((2R,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-4-(pyridin-4-ylmethoxy)-piperidine-2-carboxylic acid tert-butylamide 

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