2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-(4-methoxy-phenoxy)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-(4-methoxy-phenoxy)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester
• CAS No.: 157117-12-9
• Molecular Formula: C₂₆H₄₂O₄
• Molecular Weight: 418.617

Synonyms:2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-(4-methoxy-phenoxy)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester

Chemical Property of 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-(4-methoxy-phenoxy)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-(4-methoxy-phenoxy)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester

There total 26 articles about 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-(4-methoxy-phenoxy)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl 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: 93.0%

2,2-Dimethyl-butyric acid (1S,2R,5S,6S)-6-[2-(4-methoxy-phenoxy)-ethyl]-5-methyl-2-propyl-cyclohex-3-enylmethyl ester (157117-11-8) → 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-(4-methoxy-phenoxy)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester (157117-12-9)

Guidance literature:

With hydrogen; Rh/Al₂O₃; In toluene; at 0 ℃;

DOI:10.1016/S0040-4039(00)75797-2

Reference yield: 83.0%

2,2-Dimethyl-butyric acid (1R,2S,5R,6S)-2-[2-(4-methoxy-phenoxy)-ethyl]-5-phenylcarbamoyloxy-6-propyl-cyclohex-3-enylmethyl ester (157117-10-7) → 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-(4-methoxy-phenoxy)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester (157117-12-9) + 2,2-Dimethyl-butyric acid (1S,2R,5S,6S)-6-[2-(4-methoxy-phenoxy)-ethyl]-5-methyl-2-propyl-cyclohex-3-enylmethyl ester (157117-11-8)

Guidance literature:

With Me₅Cu₃Li₂; In diethyl ether; Yields of byproduct given;

DOI:10.1016/S0040-4039(00)75797-2

Reference yield:

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose (33208-47-8) → 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-(4-methoxy-phenoxy)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester (157117-12-9)

Guidance literature:

Multi-step reaction with 24 steps

1: diethyl ether / Ambient temperature

2: Et₃N / DMAP / CH₂Cl₂ / Ambient temperature

4: DEAD-Ph₃P / CH₂Cl₂ / Ambient temperature

5: H₂ / Pd/C / methanol

6: Et₃N / CH₂Cl₂ / -10 °C

7: MeONa / methanol / Ambient temperature

8: diethyl ether / Ambient temperature

9: H₂ / Pd/C / methanol

10: H⁽¹⁺⁾

11: pyridine

12: Swern oxidation

13: MeLi / tetrahydrofuran / -78 °C

14: methylaluminum bis-(4-bromo-2,6-di-tert-butyl-phenoxide) (MABR) / CH₂Cl₂ / -78 °C

15: NaBH₄ / 0.25 h / -20 °C

16: 92 percent / MsCl, Et₃N, DMAP / CH₂Cl₂

17: Bu₄NF / tetrahydrofuran

18: Bu₃P / tetrahydrofuran / 1 h / Ambient temperature

19: 1.) NaIO₄; 2.) Et₃N / 1.) MeOH; 2.) PhCH₃, reflux

20: 86 percent / Hg(OTFA)2 / H₂O; acetone / 1 h / slow addition of the substrate to catalyst

21: 93 percent / MsCl, Et₃N / CH₂Cl₂ / -10 deg C up to RT

22: CeCl₃*7H₂O, NaBH₄ / methanol

23: 98 percent / DMAP/pyridine

24: Me₅Cu₃Li₂ / diethyl ether

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; tributylphosphine; Me₅Cu₃Li₂; tetrabutyl ammonium fluoride; methyllithium; hydrogen; sodium methylate; hydrogen cation; methanesulfonyl chloride; methylaluminium bis(4-bromo-2,6-di-tert.-butylphenoxide); triethylamine; triphenylphosphine; diethylazodicarboxylate; dmap; palladium on activated charcoal; mercury(II) trifluoroacetate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone;

DOI:10.1016/S0040-4039(00)75797-2

upstream raw materials:

2,2-Dimethyl-butyric acid (1S,2R,5S,6S)-6-[2-(4-methoxy-phenoxy)-ethyl]-5-methyl-2-propyl-cyclohex-3-enylmethyl ester

2,2-Dimethyl-butyric acid (1R,2S,5R,6S)-2-[2-(4-methoxy-phenoxy)-ethyl]-5-phenylcarbamoyloxy-6-propyl-cyclohex-3-enylmethyl ester

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose

1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(2-propenyl)-β-D-glucopyranose

Downstream raw materials:

2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-3-methyl-2-(2-oxo-ethyl)-6-propyl-cyclohexylmethyl ester

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