(-)-(3aR,5aR,6S,9R,10aR,Z)-8-(tert-butyldiphenylsilyloxymethyl)-6-hydroxy-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,9,10,10a-decahydrocyclohepta[e]inden-9-yl benzoate

Base Information

• Chemical Name: (-)-(3aR,5aR,6S,9R,10aR,Z)-8-(tert-butyldiphenylsilyloxymethyl)-6-hydroxy-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,9,10,10a-decahydrocyclohepta[e]inden-9-yl benzoate
• CAS No.: 925688-51-3
• Molecular Formula: C₄₃H₅₄O₄Si
• Molecular Weight: 662.985
• Mol file: 925688-51-3.mol

Synonyms:(-)-(3aR,5aR,6S,9R,10aR,Z)-8-(tert-butyldiphenylsilyloxymethyl)-6-hydroxy-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,9,10,10a-decahydrocyclohepta[e]inden-9-yl benzoate

Chemical Property of (-)-(3aR,5aR,6S,9R,10aR,Z)-8-(tert-butyldiphenylsilyloxymethyl)-6-hydroxy-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,9,10,10a-decahydrocyclohepta[e]inden-9-yl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(3aR,5aR,6S,9R,10aR,Z)-8-(tert-butyldiphenylsilyloxymethyl)-6-hydroxy-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,9,10,10a-decahydrocyclohepta[e]inden-9-yl benzoate

There total 22 articles about (-)-(3aR,5aR,6S,9R,10aR,Z)-8-(tert-butyldiphenylsilyloxymethyl)-6-hydroxy-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,9,10,10a-decahydrocyclohepta[e]inden-9-yl benzoate 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: 95.0%

(-)-(3aR,5aR,9R,10aR,Z)-8-(tert-butyldiphenylsilyloxymethyl)-1-isopropyl-3a,5a-dimethyl-6-oxo-2,3,3a,4,5,5a,6,9,10,10a-decahydrocyclohepta[e]inden-9-yl benzoate (925688-50-2) → (-)-(3aR,5aR,6S,9R,10aR,Z)-8-(tert-butyldiphenylsilyloxymethyl)-6-hydroxy-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,9,10,10a-decahydrocyclohepta[e]inden-9-yl benzoate (925688-51-3)

Guidance literature:

With dimethylsulfide borane complex; (R)-CBS catalyst; In dichloromethane; toluene; at -40 ℃; for 2h;

DOI:10.1021/ol0628816

Reference yield:

(+)-(3aS,5aS,6S,9aR,9bR)-6-(4-methoxybenzyloxy)-decahydro-9a-hydroxy-3a,5a-dimethyl-2H-cyclopenta[a]naphthalen-1(9bH)-one (824940-70-7) → (-)-(3aR,5aR,6S,9R,10aR,Z)-8-(tert-butyldiphenylsilyloxymethyl)-6-hydroxy-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,9,10,10a-decahydrocyclohepta[e]inden-9-yl benzoate (925688-51-3)

Guidance literature:

Multi-step reaction with 21 steps

1.1: SOCl₂; pyridine / CH₂Cl₂ / 2 h / 20 °C

1.2: 92 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 24 h / Heating

2.1: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H₂O; CH₂Cl₂; 2-methyl-propan-2-ol / 2 h / 20 °C

3.1: 94 percent / SmI₂; hexamethylphosphoramide / tetrahydrofuran / 1 h / 20 °C

4.1: 84 percent / CeCl₃ / tetrahydrofuran; diethyl ether / 2 h / -78 °C

5.1: 95 percent / hydrogen / Pd/C / ethyl acetate / 1.5 h / 20 °C / 760 Torr

6.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

7.1: 100 percent / SOCl₂; pyridine / CH₂Cl₂ / 2 h / 20 °C

8.1: 100 percent / p-TsOH / benzene / 4 h / Heating

9.1: LHMDS / hexane; tetrahydrofuran / -78 - 0 °C

9.2: 79 percent / hexane; tetrahydrofuran / 1 h / -78 °C

10.1: 66 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

11.1: 81 percent / SmI₂; hexamethylphosphoramide / tetrahydrofuran / 1 h / -78 °C

12.1: triethylamine / CH₂Cl₂ / 2 h / 0 °C

13.1: PhSeCl / tetrahydrofuran / 0.25 h / -78 °C

13.2: 16.1 mg / pyridine; H₂O₂ / tetrahydrofuran; H₂O / 1 h / 0 °C

14.1: 98 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 6 h / Heating

15.1: DIBAL-H / CH₂Cl₂; hexane / 2 h / -78 °C

16.1: VO(acac)2; tert-butyl hydroperoxide / toluene / 3 h / -40 °C

17.1: imidazole / CH₂Cl₂ / 3 h / 20 °C

18.1: 17.6 mg / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

19.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 24 h / 50 °C

20.1: 15.7 mg / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 24 h / 50 °C

21.1: 95 percent / BH₃*SMe₂; (R)-CBS catalyst / CH₂Cl₂; toluene / 2 h / -40 °C

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; thionyl chloride; Phenylselenyl chloride; samarium diiodide; cerium(III) chloride; bis(acetylacetonate)oxovanadium; dimethylsulfide borane complex; (R)-CBS catalyst; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol; benzene; 6.1: Dess-Martin oxidation / 18.1: Dess-Martin oxidation;

DOI:10.1021/ol0628816

Reference yield:

(+)-(3aS,5aR,6S)-6-(4-methoxybenzyloxy)-2,3,3a,4,5,5a,6,7,8,9-decahydro-3a,5a-dimethyl-cyclopenta[a]naphthalen-1-one (824940-72-9) → (-)-(3aR,5aR,6S,9R,10aR,Z)-8-(tert-butyldiphenylsilyloxymethyl)-6-hydroxy-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,9,10,10a-decahydrocyclohepta[e]inden-9-yl benzoate (925688-51-3)

Guidance literature:

Multi-step reaction with 20 steps

1.1: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H₂O; CH₂Cl₂; 2-methyl-propan-2-ol / 2 h / 20 °C

2.1: 94 percent / SmI₂; hexamethylphosphoramide / tetrahydrofuran / 1 h / 20 °C

3.1: 84 percent / CeCl₃ / tetrahydrofuran; diethyl ether / 2 h / -78 °C

4.1: 95 percent / hydrogen / Pd/C / ethyl acetate / 1.5 h / 20 °C / 760 Torr

5.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

6.1: 100 percent / SOCl₂; pyridine / CH₂Cl₂ / 2 h / 20 °C

7.1: 100 percent / p-TsOH / benzene / 4 h / Heating

8.1: LHMDS / hexane; tetrahydrofuran / -78 - 0 °C

8.2: 79 percent / hexane; tetrahydrofuran / 1 h / -78 °C

9.1: 66 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

10.1: 81 percent / SmI₂; hexamethylphosphoramide / tetrahydrofuran / 1 h / -78 °C

11.1: triethylamine / CH₂Cl₂ / 2 h / 0 °C

12.1: PhSeCl / tetrahydrofuran / 0.25 h / -78 °C

12.2: 16.1 mg / pyridine; H₂O₂ / tetrahydrofuran; H₂O / 1 h / 0 °C

13.1: 98 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 6 h / Heating

14.1: DIBAL-H / CH₂Cl₂; hexane / 2 h / -78 °C

15.1: VO(acac)2; tert-butyl hydroperoxide / toluene / 3 h / -40 °C

16.1: imidazole / CH₂Cl₂ / 3 h / 20 °C

17.1: 17.6 mg / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

18.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 24 h / 50 °C

19.1: 15.7 mg / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 24 h / 50 °C

20.1: 95 percent / BH₃*SMe₂; (R)-CBS catalyst / CH₂Cl₂; toluene / 2 h / -40 °C

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; thionyl chloride; Phenylselenyl chloride; samarium diiodide; cerium(III) chloride; bis(acetylacetonate)oxovanadium; dimethylsulfide borane complex; (R)-CBS catalyst; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol; benzene; 5.1: Dess-Martin oxidation / 17.1: Dess-Martin oxidation;

DOI:10.1021/ol0628816

upstream raw materials:

(-)-(3aR,5aR,9R,10aR,Z)-8-(tert-butyldiphenylsilyloxymethyl)-1-isopropyl-3a,5a-dimethyl-6-oxo-2,3,3a,4,5,5a,6,9,10,10a-decahydrocyclohepta[e]inden-9-yl benzoate

(-)-(3aS,5aR,6S)-2,3,3a,4,5,5a,6,7,8,9-decahydro-6-hydroxy-3a,5a-dimethylcyclopenta[a]naphthalen-1-one

(+)-(3aS,5aR,6S)-6-(4-methoxybenzyloxy)-2,3,3a,4,5,5a,6,7,8,9-decahydro-3a,5a-dimethyl-cyclopenta[a]naphthalen-1-one

(+)-(3aS,5aS,6S,9aR,9bR)-6-(4-methoxybenzyloxy)-decahydro-9a-hydroxy-3a,5a-dimethyl-2H-cyclopenta[a]naphthalen-1(9bH)-one

Downstream raw materials:

(3aR,5aR,6S,9R,10aR,Z)-6-((2S,3R,4S,5R)-3,5-bis(4-methoxybenzyloxy)-4-triethylsilyloxy-tetrahydro-2H-pyran-2-yloxy)-8-((tert-butyldiphenylsilyloxy)methyl)-1-isopropyl-3a,5a-dimethyl-2,3,3a,4,5,5a,6,9,10,10a-decahydrocyclohepta[e]inden-9-yl benzoate