(-)-(3aR,5aR,8R,9R,10aR)-2,3,3a,4,5,5a,6,7,8,9,10,10a-dodecahydro-8,9-epoxy-8-(tert-butyldiphenylsilyloxymethyl)-1-isopropyl-3a,5a-dimethylcyclohepta[e]inden-6(7H)-one

Base Information

Chemical Name:(-)-(3aR,5aR,8R,9R,10aR)-2,3,3a,4,5,5a,6,7,8,9,10,10a-dodecahydro-8,9-epoxy-8-(tert-butyldiphenylsilyloxymethyl)-1-isopropyl-3a,5a-dimethylcyclohepta[e]inden-6(7H)-one
CAS No.:925688-49-9
Molecular Formula:C₃₆H₄₈O₃Si
Molecular Weight:556.861
Hs Code.:

(-)-(3aR,5aR,8R,9R,10aR)-2,3,3a,4,5,5a,6,7,8,9,10,10a-dodecahydro-8,9-epoxy-8-(tert-butyldiphenylsilyloxymethyl)-1-isopropyl-3a,5a-dimethylcyclohepta[e]inden-6(7H)-one

Synonyms:(-)-(3aR,5aR,8R,9R,10aR)-2,3,3a,4,5,5a,6,7,8,9,10,10a-dodecahydro-8,9-epoxy-8-(tert-butyldiphenylsilyloxymethyl)-1-isopropyl-3a,5a-dimethylcyclohepta[e]inden-6(7H)-one

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Chemical Property of (-)-(3aR,5aR,8R,9R,10aR)-2,3,3a,4,5,5a,6,7,8,9,10,10a-dodecahydro-8,9-epoxy-8-(tert-butyldiphenylsilyloxymethyl)-1-isopropyl-3a,5a-dimethylcyclohepta[e]inden-6(7H)-one

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Technology Process of (-)-(3aR,5aR,8R,9R,10aR)-2,3,3a,4,5,5a,6,7,8,9,10,10a-dodecahydro-8,9-epoxy-8-(tert-butyldiphenylsilyloxymethyl)-1-isopropyl-3a,5a-dimethylcyclohepta[e]inden-6(7H)-one

There total 19 articles about (-)-(3aR,5aR,8R,9R,10aR)-2,3,3a,4,5,5a,6,7,8,9,10,10a-dodecahydro-8,9-epoxy-8-(tert-butyldiphenylsilyloxymethyl)-1-isopropyl-3a,5a-dimethylcyclohepta[e]inden-6(7H)-one 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:

: C₃₆H₅₀O₃Si

: 925688-49-9
(-)-(3aR,5aR,8R,9R,10aR)-2,3,3a,4,5,5a,6,7,8,9,10,10a-dodecahydro-8,9-epoxy-8-(tert-butyldiphenylsilyloxymethyl)-1-isopropyl-3a,5a-dimethylcyclohepta[e]inden-6(7H)-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/ol0628816

Reference yield:

: 824940-72-9
(+)-(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

: 925688-49-9
(-)-(3aR,5aR,8R,9R,10aR)-2,3,3a,4,5,5a,6,7,8,9,10,10a-dodecahydro-8,9-epoxy-8-(tert-butyldiphenylsilyloxymethyl)-1-isopropyl-3a,5a-dimethylcyclohepta[e]inden-6(7H)-one

Guidance literature:: Multi-step reaction with 17 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

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; thionyl chloride; Phenylselenyl chloride; samarium diiodide; cerium(III) chloride; bis(acetylacetonate)oxovanadium; 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

Reference yield:

: 925688-45-5
(-)-(3aS,5aR,6S)-2,3,3a,4,5,5a,6,7,8,9-decahydro-6-hydroxy-3a,5a-dimethylcyclopenta[a]naphthalen-1-one

: 925688-49-9
(-)-(3aR,5aR,8R,9R,10aR)-2,3,3a,4,5,5a,6,7,8,9,10,10a-dodecahydro-8,9-epoxy-8-(tert-butyldiphenylsilyloxymethyl)-1-isopropyl-3a,5a-dimethylcyclohepta[e]inden-6(7H)-one

Guidance literature:: Multi-step reaction with 16 steps

1.1: 94 percent / SmI₂; hexamethylphosphoramide / tetrahydrofuran / 1 h / 20 °C

2.1: 84 percent / CeCl₃ / tetrahydrofuran; diethyl ether / 2 h / -78 °C

3.1: 95 percent / hydrogen / Pd/C / ethyl acetate / 1.5 h / 20 °C / 760 Torr

4.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

5.1: 100 percent / SOCl₂; pyridine / CH₂Cl₂ / 2 h / 20 °C

6.1: 100 percent / p-TsOH / benzene / 4 h / Heating

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

7.2: 79 percent / hexane; tetrahydrofuran / 1 h / -78 °C

8.1: 66 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

9.1: 81 percent / SmI₂; hexamethylphosphoramide / tetrahydrofuran / 1 h / -78 °C

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

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

11.2: 16.1 mg / pyridine; H₂O₂ / tetrahydrofuran; H₂O / 1 h / 0 °C

12.1: 98 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 6 h / Heating

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

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

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

16.1: 17.6 mg / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; thionyl chloride; Phenylselenyl chloride; samarium diiodide; cerium(III) chloride; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene; benzene; 4.1: Dess-Martin oxidation / 16.1: Dess-Martin oxidation;
DOI:10.1021/ol0628816