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

Base Information

Chemical Name:(2R,3S)-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-(1-ethoxyethoxy)-1-butanol
CAS No.:1054638-88-8
Molecular Formula:C₁₉H₃₇NO₅
Molecular Weight:359.506
Hs Code.:

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

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

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

There total 11 articles about (2R,3S)-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-(1-ethoxyethoxy)-1-butanol 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: 89.0%

: 1054810-89-7
(2R,3S)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-(1-ethoxyethoxy)butane

: 1054638-88-8
(2R,3S)-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-(1-ethoxyethoxy)-1-butanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.166667h;
DOI:10.1021/jo960351p

Reference yield:

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

: 1054638-88-8
(2R,3S)-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-(1-ethoxyethoxy)-1-butanol

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene; 1: Hydrogenolysis / 2: silylation / 3: Mitsunobu reaction / 4: Reduction / 5: Addition / 6: desilylation;
DOI:10.1021/jo960351p

Reference yield:

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

: 1054638-88-8
(2R,3S)-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-(1-ethoxyethoxy)-1-butanol

Guidance literature:: Multi-step reaction with 8 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

With 1H-imidazole; diisopropoxytitanium diazide; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; triphenylphosphine; diethylazodicarboxylate; titanium(IV) isopropylate; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 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;
DOI:10.1021/jo960351p