*,S^*)>-β-<<(1,1-dimethylethoxy)carbonyl>amino>-α-hydroxycyclohexanebutanoic acid, ethyl ester

Base Information

• Chemical Name: *,S^*)>-β-<<(1,1-dimethylethoxy)carbonyl>amino>-α-hydroxycyclohexanebutanoic acid, ethyl ester
• CAS No.: 133485-22-0
• Molecular Formula: C₁₇H₃₁NO₅
• Molecular Weight: 329.437

Synonyms:*,S^*)>-β-<<(1,1-dimethylethoxy)carbonyl>amino>-α-hydroxycyclohexanebutanoic acid, ethyl ester

Chemical Property of *,S^*)>-β-<<(1,1-dimethylethoxy)carbonyl>amino>-α-hydroxycyclohexanebutanoic acid, ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of *,S^*)>-β-<<(1,1-dimethylethoxy)carbonyl>amino>-α-hydroxycyclohexanebutanoic acid, ethyl ester

There total 19 articles about *,S^*)>-β-<<(1,1-dimethylethoxy)carbonyl>amino>-α-hydroxycyclohexanebutanoic acid, ethyl ester 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: 82.0%

*,S*)>-β-<<(1,1-dimethylethoxy)carbonyl>amino>-α-cyclohexanepropanol (151521-07-2) → *,S*)>-β-<<(1,1-dimethylethoxy)carbonyl>amino>-α-hydroxycyclohexanebutanoic acid, ethyl ester (133485-22-0)

Guidance literature:

With mercury dichloride; mercury(II) oxide; In ethanol; for 72h; Ambient temperature;

DOI:10.1021/jm00069a001

Reference yield: 55.0%

((S)-1-Cyclohexylmethyl-2-hydroxy-3,3,3-tris-methylsulfanyl-propyl)-carbamic acid tert-butyl ester (1046536-27-9) → *,R*)>-β-<<(1,1-dimethylethoxy)carbonyl>amino>-α-hydroxycyclohexanebutanoic acid, ethyl ester (151521-08-3) + *,S*)>-β-<<(1,1-dimethylethoxy)carbonyl>amino>-α-hydroxycyclohexanebutanoic acid, ethyl ester (133485-22-0)

Guidance literature:

With mercury dichloride; mercury(II) oxide; In ethanol; at 25 ℃; for 36h;

DOI:10.1021/jm00069a001

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → *,S*)>-β-<<(1,1-dimethylethoxy)carbonyl>amino>-α-hydroxycyclohexanebutanoic acid, ethyl ester (133485-22-0)

Guidance literature:

Multi-step reaction with 9 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

9: HCl; H₂O / tetrahydrofuran / 5 h

With 1H-imidazole; hydrogenchloride; sodium periodate; tetrabutyl ammonium fluoride; water; 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 / 9: Hydrolysis;

DOI:10.1021/jo960351p

upstream raw materials:

((S)-1-Cyclohexylmethyl-2-hydroxy-3,3,3-tris-methylsulfanyl-propyl)-carbamic acid tert-butyl ester

*,S^*)>-β-<<(1,1-dimethylethoxy)carbonyl>amino>-α-cyclohexanepropanol

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

di-tert-butyl dicarbonate

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