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

Base Information

Chemical Name:2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-3-methyl-2-(2-oxo-ethyl)-6-propyl-cyclohexylmethyl ester
CAS No.:156741-10-5
Molecular Formula:C₁₉H₃₄O₃
Molecular Weight:310.477
Hs Code.:

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

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

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

There total 25 articles about 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-3-methyl-2-(2-oxo-ethyl)-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: 88.0%

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

: 156741-10-5
2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-3-methyl-2-(2-oxo-ethyl)-6-propyl-cyclohexylmethyl ester

Guidance literature:: With 4 Angstroem MS; pyridinium chlorochromate; In dichloromethane;
DOI:10.1016/S0040-4039(00)75797-2

Reference yield:

: 33208-47-8
4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose

: 156741-10-5
2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-3-methyl-2-(2-oxo-ethyl)-6-propyl-cyclohexylmethyl ester

Guidance literature:: Multi-step reaction with 26 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

25: 96 percent / CAN / acetonitrile; H₂O

26: 88 percent / PCC, 4 Angstroem MS / CH₂Cl₂

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; ammonium cerium(IV) nitrate; tributylphosphine; 4 Angstroem MS; Me₅Cu₃Li₂; tetrabutyl ammonium fluoride; methyllithium; hydrogen; sodium methylate; hydrogen cation; methanesulfonyl chloride; methylaluminium bis(4-bromo-2,6-di-tert.-butylphenoxide); triethylamine; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; dmap; palladium on activated charcoal; mercury(II) trifluoroacetate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; acetonitrile;
DOI:10.1016/S0040-4039(00)75797-2

Reference yield:

: 104206-19-1
1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(2-propenyl)-β-D-glucopyranose

: 156741-10-5
2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-3-methyl-2-(2-oxo-ethyl)-6-propyl-cyclohexylmethyl ester

Guidance literature:: Multi-step reaction with 25 steps

1: Et₃N / DMAP / CH₂Cl₂ / Ambient temperature

3: DEAD-Ph₃P / CH₂Cl₂ / Ambient temperature

4: H₂ / Pd/C / methanol

5: Et₃N / CH₂Cl₂ / -10 °C

6: MeONa / methanol / Ambient temperature

7: diethyl ether / Ambient temperature

8: H₂ / Pd/C / methanol

9: H⁽¹⁺⁾

10: pyridine

11: Swern oxidation

12: MeLi / tetrahydrofuran / -78 °C

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

14: NaBH₄ / 0.25 h / -20 °C

15: 92 percent / MsCl, Et₃N, DMAP / CH₂Cl₂

16: Bu₄NF / tetrahydrofuran

17: Bu₃P / tetrahydrofuran / 1 h / Ambient temperature

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

19: 86 percent / Hg(OTFA)2 / H₂O; acetone / 1 h / slow addition of the substrate to catalyst

20: 93 percent / MsCl, Et₃N / CH₂Cl₂ / -10 deg C up to RT

21: CeCl₃*7H₂O, NaBH₄ / methanol

22: 98 percent / DMAP/pyridine

23: Me₅Cu₃Li₂ / diethyl ether

24: 96 percent / CAN / acetonitrile; H₂O

25: 88 percent / PCC, 4 Angstroem MS / CH₂Cl₂

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; ammonium cerium(IV) nitrate; tributylphosphine; 4 Angstroem MS; Me₅Cu₃Li₂; tetrabutyl ammonium fluoride; methyllithium; hydrogen; sodium methylate; hydrogen cation; methanesulfonyl chloride; methylaluminium bis(4-bromo-2,6-di-tert.-butylphenoxide); triethylamine; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; dmap; palladium on activated charcoal; mercury(II) trifluoroacetate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; acetonitrile;
DOI:10.1016/S0040-4039(00)75797-2