ethyl (2R,3S)-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-(1-ethoxyethoxy)butanoate

Base Information

Chemical Name:ethyl (2R,3S)-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-(1-ethoxyethoxy)butanoate
CAS No.:1053738-27-4
Molecular Formula:C₂₁H₃₉NO₆
Molecular Weight:401.544
Hs Code.:

Synonyms:ethyl (2R,3S)-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-(1-ethoxyethoxy)butanoate

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Chemical Property of ethyl (2R,3S)-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-(1-ethoxyethoxy)butanoate

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Technology Process of ethyl (2R,3S)-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-(1-ethoxyethoxy)butanoate

There total 12 articles about ethyl (2R,3S)-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-(1-ethoxyethoxy)butanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 1053738-27-4
ethyl (2R,3S)-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-(1-ethoxyethoxy)butanoate

Guidance literature:: Multi-step reaction with 8 steps

1: 85 percent / H₂ / Pd(OH)2/C / ethyl acetate / 760 Torr

2: 83 percent / imidazole / dimethylformamide / 48 h / 20 °C

3: 89 percent / PPh₃; diethyl azodicarboxylate / benzene / 12 h / 20 °C

4: 71 percent / DIBALH / CH₂Cl₂; hexane / 2 h / -20 °C

5: 83 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 20 °C

6: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C

7: 86 percent / NaIO₄; NaHCO₃ / RuCl₃ / acetonitrile; CCl₄; H₂O / 48 h / 20 °C

8: toluene / 24 h / Heating

With 1H-imidazole; sodium periodate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; triphenylphosphine; diethylazodicarboxylate; ruthenium trichloride; palladium dihydroxide; In tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 1: Hydrogenolysis / 2: silylation / 3: Mitsunobu reaction / 4: Reduction / 5: Addition / 6: desilylation / 7: Oxidation / 8: Esterification;
DOI:10.1021/jo960351p

Reference yield:

: 1589-44-2
(E)-4-cyclohexyl-2-buten-1-ol

: 1053738-27-4
ethyl (2R,3S)-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-(1-ethoxyethoxy)butanoate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 4 Angstroem molecular sieves; D-(-)-diisopropyl tartrate / titanium tetraisopropoxide / CH₂Cl₂ / 0.5 h / -20 °C

1.2: tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 24 h / -20 °C

2.1: 99 percent / titanium diazidodiisopropoxide / benzene / 0.13 h / 75 °C

3.1: 97 percent / H₂ / Pd/C / ethyl acetate / 18 h / 760 Torr

4.1: 83 percent / imidazole / dimethylformamide / 48 h / 20 °C

5.1: 89 percent / PPh₃; diethyl azodicarboxylate / benzene / 12 h / 20 °C

6.1: 71 percent / DIBALH / CH₂Cl₂; hexane / 2 h / -20 °C

7.1: 83 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 20 °C

8.1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C

9.1: 86 percent / NaIO₄; NaHCO₃ / RuCl₃ / acetonitrile; CCl₄; H₂O / 48 h / 20 °C

10.1: toluene / 24 h / Heating

With 1H-imidazole; sodium periodate; diisopropoxytitanium diazide; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; triphenylphosphine; diethylazodicarboxylate; titanium(IV) isopropylate; ruthenium trichloride; palladium on activated charcoal; In tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 1.1: Sharpless epoxidation / 1.2: Sharpless epoxidation / 2.1: Ring cleavage / 3.1: Hydrogenolysis / 4.1: silylation / 5.1: Mitsunobu reaction / 6.1: Reduction / 7.1: Addition / 8.1: desilylation / 9.1: Oxidation / 10.1: Esterification;
DOI:10.1021/jo960351p

Reference yield:

: 105198-42-3,105198-39-8
ethyl (2E)-4-cyclohexyl-2-butenoate

: 1053738-27-4
ethyl (2R,3S)-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-(1-ethoxyethoxy)butanoate

Guidance literature:: Multi-step reaction with 11 steps

1.1: 6.77 g / DIBALH / diethyl ether; hexane / 0.5 h / -78 °C

2.1: 4 Angstroem molecular sieves; D-(-)-diisopropyl tartrate / titanium tetraisopropoxide / CH₂Cl₂ / 0.5 h / -20 °C

2.2: tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 24 h / -20 °C

3.1: 99 percent / titanium diazidodiisopropoxide / benzene / 0.13 h / 75 °C

4.1: 97 percent / H₂ / Pd/C / ethyl acetate / 18 h / 760 Torr

5.1: 83 percent / imidazole / dimethylformamide / 48 h / 20 °C

6.1: 89 percent / PPh₃; diethyl azodicarboxylate / benzene / 12 h / 20 °C

7.1: 71 percent / DIBALH / CH₂Cl₂; hexane / 2 h / -20 °C

8.1: 83 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 20 °C

9.1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C

10.1: 86 percent / NaIO₄; NaHCO₃ / RuCl₃ / acetonitrile; CCl₄; H₂O / 48 h / 20 °C

11.1: toluene / 24 h / Heating

With 1H-imidazole; sodium periodate; diisopropoxytitanium diazide; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; triphenylphosphine; diethylazodicarboxylate; titanium(IV) isopropylate; ruthenium trichloride; palladium on activated charcoal; In tetrahydrofuran; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 1.1: Reduction / 2.1: Sharpless epoxidation / 2.2: Sharpless epoxidation / 3.1: Ring cleavage / 4.1: Hydrogenolysis / 5.1: silylation / 6.1: Mitsunobu reaction / 7.1: Reduction / 8.1: Addition / 9.1: desilylation / 10.1: Oxidation / 11.1: Esterification;
DOI:10.1021/jo960351p