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

Base Information

• Chemical Name: 2,2-Dimethyl-butyric acid (1R,2S,5S,6S)-5-hydroxy-2-[2-(4-methoxy-phenoxy)-ethyl]-6-propyl-cyclohex-3-enylmethyl ester
• CAS No.: 157238-44-3
• Molecular Formula: C₂₅H₃₈O₅
• Molecular Weight: 418.574
• Mol file: 157238-44-3.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 20 articles about 2,2-Dimethyl-butyric acid (1R,2S,5S,6S)-5-hydroxy-2-[2-(4-methoxy-phenoxy)-ethyl]-6-propyl-cyclohex-3-enylmethyl 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:

Acetic acid (1R,2S,3R,4R,5R)-4-allyl-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester (157116-97-7) → 2,2-Dimethyl-butyric acid (1R,2S,5S,6S)-5-hydroxy-2-[2-(4-methoxy-phenoxy)-ethyl]-6-propyl-cyclohex-3-enylmethyl ester (157238-44-3)

Guidance literature:

Multi-step reaction with 20 steps

2: DEAD-Ph₃P / CH₂Cl₂ / Ambient temperature

3: H₂ / Pd/C / methanol

4: Et₃N / CH₂Cl₂ / -10 °C

5: MeONa / methanol / Ambient temperature

6: diethyl ether / Ambient temperature

7: H₂ / Pd/C / methanol

8: H⁽¹⁺⁾

9: pyridine

10: Swern oxidation

11: MeLi / tetrahydrofuran / -78 °C

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

13: NaBH₄ / 0.25 h / -20 °C

14: 92 percent / MsCl, Et₃N, DMAP / CH₂Cl₂

15: Bu₄NF / tetrahydrofuran

16: Bu₃P / tetrahydrofuran / 1 h / Ambient temperature

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

18: 86 percent / Hg(OTFA)2 / H₂O; acetone / 1 h / slow addition of the substrate to catalyst

19: 93 percent / MsCl, Et₃N / CH₂Cl₂ / -10 deg C up to RT

20: CeCl₃*7H₂O, NaBH₄ / methanol

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

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

Reference yield:

Acetic acid (1R,2S,3R,4R,5R)-2-benzyloxy-4-(2-hydroxy-ethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester → 2,2-Dimethyl-butyric acid (1R,2S,5S,6S)-5-hydroxy-2-[2-(4-methoxy-phenoxy)-ethyl]-6-propyl-cyclohex-3-enylmethyl ester (157238-44-3)

Guidance literature:

Multi-step reaction with 19 steps

1: DEAD-Ph₃P / CH₂Cl₂ / Ambient temperature

2: H₂ / Pd/C / methanol

3: Et₃N / CH₂Cl₂ / -10 °C

4: MeONa / methanol / Ambient temperature

5: diethyl ether / Ambient temperature

6: H₂ / Pd/C / methanol

7: H⁽¹⁺⁾

8: pyridine

9: Swern oxidation

10: MeLi / tetrahydrofuran / -78 °C

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

12: NaBH₄ / 0.25 h / -20 °C

13: 92 percent / MsCl, Et₃N, DMAP / CH₂Cl₂

14: Bu₄NF / tetrahydrofuran

15: Bu₃P / tetrahydrofuran / 1 h / Ambient temperature

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

17: 86 percent / Hg(OTFA)2 / H₂O; acetone / 1 h / slow addition of the substrate to catalyst

18: 93 percent / MsCl, Et₃N / CH₂Cl₂ / -10 deg C up to RT

19: CeCl₃*7H₂O, NaBH₄ / methanol

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

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

Reference yield:

(2S,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-[2-(4-methoxy-phenoxy)-ethyl]-3-propyl-tetrahydro-pyran-4-ol (157117-01-6) → 2,2-Dimethyl-butyric acid (1R,2S,5S,6S)-5-hydroxy-2-[2-(4-methoxy-phenoxy)-ethyl]-6-propyl-cyclohex-3-enylmethyl ester (157238-44-3)

Guidance literature:

Multi-step reaction with 11 steps

1: Swern oxidation

2: MeLi / tetrahydrofuran / -78 °C

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

4: NaBH₄ / 0.25 h / -20 °C

5: 92 percent / MsCl, Et₃N, DMAP / CH₂Cl₂

6: Bu₄NF / tetrahydrofuran

7: Bu₃P / tetrahydrofuran / 1 h / Ambient temperature

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

9: 86 percent / Hg(OTFA)2 / H₂O; acetone / 1 h / slow addition of the substrate to catalyst

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

11: CeCl₃*7H₂O, NaBH₄ / methanol

With dmap; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; tributylphosphine; tetrabutyl ammonium fluoride; methyllithium; methanesulfonyl chloride; methylaluminium bis(4-bromo-2,6-di-tert.-butylphenoxide); triethylamine; mercury(II) trifluoroacetate; In tetrahydrofuran; methanol; dichloromethane; water; acetone;

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

upstream raw materials:

2,2-Dimethyl-butyric acid (1R,2S,6S)-2-[2-(4-methoxy-phenoxy)-ethyl]-5-oxo-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

Acetic acid (1R,2S,3R,4R,5R)-4-allyl-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester

Downstream raw materials:

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