(3S,3aS,5R,5aR,7S,10aS,12aS,12bR)-7-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,5,5a,7,8,9,10,11,12,12b-tetradecahydro-10a,12a-epoxybenzo[4,5]cyclohepta-[1,2-e]inden-5-ol

Base Information

Chemical Name:(3S,3aS,5R,5aR,7S,10aS,12aS,12bR)-7-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,5,5a,7,8,9,10,11,12,12b-tetradecahydro-10a,12a-epoxybenzo[4,5]cyclohepta-[1,2-e]inden-5-ol
CAS No.:1311175-05-9
Molecular Formula:C₃₇H₅₀O₅Si
Molecular Weight:602.886
Hs Code.:

(3S,3aS,5R,5aR,7S,10aS,12aS,12bR)-7-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,5,5a,7,8,9,10,11,12,12b-tetradecahydro-10a,12a-epoxybenzo[4,5]cyclohepta-[1,2-e]inden-5-ol

Synonyms:(3S,3aS,5R,5aR,7S,10aS,12aS,12bR)-7-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,5,5a,7,8,9,10,11,12,12b-tetradecahydro-10a,12a-epoxybenzo[4,5]cyclohepta-[1,2-e]inden-5-ol

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Chemical Property of (3S,3aS,5R,5aR,7S,10aS,12aS,12bR)-7-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,5,5a,7,8,9,10,11,12,12b-tetradecahydro-10a,12a-epoxybenzo[4,5]cyclohepta-[1,2-e]inden-5-ol

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Technology Process of (3S,3aS,5R,5aR,7S,10aS,12aS,12bR)-7-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,5,5a,7,8,9,10,11,12,12b-tetradecahydro-10a,12a-epoxybenzo[4,5]cyclohepta-[1,2-e]inden-5-ol

There total 21 articles about (3S,3aS,5R,5aR,7S,10aS,12aS,12bR)-7-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,5,5a,7,8,9,10,11,12,12b-tetradecahydro-10a,12a-epoxybenzo[4,5]cyclohepta-[1,2-e]inden-5-ol 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:

: C₃₅H₆₄O₇Si₂

: 1311175-05-9
(3S,3aS,5R,5aR,7S,10aS,12aS,12bR)-7-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,5,5a,7,8,9,10,11,12,12b-tetradecahydro-10a,12a-epoxybenzo[4,5]cyclohepta-[1,2-e]inden-5-ol

Guidance literature:: Multi-step reaction with 21 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 5 h

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 °C / Inert atmosphere

3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

4.1: zinc / methanol / 8 h / 20 °C / Inert atmosphere

5.1: 1H-imidazole; dmap / dichloromethane / 8 h / 20 °C / Inert atmosphere

6.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1.08 h / -78 - 20 °C / Inert atmosphere

6.2: 1.5 h / Inert atmosphere

7.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h / -20 °C / Inert atmosphere

8.1: formic acid / tetrahydrofuran; water / 2 h / 0 °C / Inert atmosphere

9.1: copper diacetate / methanol / 18 h / 20 °C / Inert atmosphere

10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 0 °C / Inert atmosphere

11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

12.1: diisobutylaluminium hydride / hexane; dichloromethane / 1.5 h / -78 °C / Inert atmosphere

13.1: pyridine; dmap / dichloromethane / 12 h / 0 °C / Inert atmosphere

14.1: chloro-trimethyl-silane; tetrabutylammomium bromide / dichloromethane / 0.31 h / 0 - 20 °C / Inert atmosphere

15.1: 1H-imidazole; 1,1,1,3,3,3-hexamethyl-disilazane / dichloromethane / 18 h / 20 °C / Inert atmosphere

16.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,3-bis-(diphenylphosphino)propane; cesium acetate; tetrabutylammonium acetate / N,N-dimethyl-formamide / 4.5 h / 20 - 70 °C / Inert atmosphere

17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

18.1: diisobutylaluminium hydride / hexane; dichloromethane / 1.5 h / -78 °C / Inert atmosphere

19.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

20.1: camphor-10-sulfonic acid / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

21.1: methanol; sodium tetrahydroborate / 1 h / 0 °C / Inert atmosphere

With pyridine; 1H-imidazole; methanol; dmap; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; chloro-trimethyl-silane; formic acid; palladium 10% on activated carbon; camphor-10-sulfonic acid; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; iodine; cesium acetate; copper diacetate; tetrabutylammonium acetate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 7.1: Rubottom oxidation / 16.1: Heck reaction / 19.1: Dess-Martin oxidation / 20.1: oxy-Michael reaction;
DOI:10.1021/ol201327u

Reference yield:

: 1311174-78-3
C₃₅H₆₆O₇Si₂

: 1311175-05-9
(3S,3aS,5R,5aR,7S,10aS,12aS,12bR)-7-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,5,5a,7,8,9,10,11,12,12b-tetradecahydro-10a,12a-epoxybenzo[4,5]cyclohepta-[1,2-e]inden-5-ol

Guidance literature:: Multi-step reaction with 20 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 °C / Inert atmosphere

2.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

3.1: zinc / methanol / 8 h / 20 °C / Inert atmosphere

4.1: 1H-imidazole; dmap / dichloromethane / 8 h / 20 °C / Inert atmosphere

5.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1.08 h / -78 - 20 °C / Inert atmosphere

5.2: 1.5 h / Inert atmosphere

6.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h / -20 °C / Inert atmosphere

7.1: formic acid / tetrahydrofuran; water / 2 h / 0 °C / Inert atmosphere

8.1: copper diacetate / methanol / 18 h / 20 °C / Inert atmosphere

9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 0 °C / Inert atmosphere

10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

11.1: diisobutylaluminium hydride / hexane; dichloromethane / 1.5 h / -78 °C / Inert atmosphere

12.1: pyridine; dmap / dichloromethane / 12 h / 0 °C / Inert atmosphere

13.1: chloro-trimethyl-silane; tetrabutylammomium bromide / dichloromethane / 0.31 h / 0 - 20 °C / Inert atmosphere

14.1: 1H-imidazole; 1,1,1,3,3,3-hexamethyl-disilazane / dichloromethane / 18 h / 20 °C / Inert atmosphere

15.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,3-bis-(diphenylphosphino)propane; cesium acetate; tetrabutylammonium acetate / N,N-dimethyl-formamide / 4.5 h / 20 - 70 °C / Inert atmosphere

16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

17.1: diisobutylaluminium hydride / hexane; dichloromethane / 1.5 h / -78 °C / Inert atmosphere

18.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

19.1: camphor-10-sulfonic acid / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

20.1: methanol; sodium tetrahydroborate / 1 h / 0 °C / Inert atmosphere

With pyridine; 1H-imidazole; methanol; dmap; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; chloro-trimethyl-silane; formic acid; camphor-10-sulfonic acid; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; iodine; cesium acetate; copper diacetate; tetrabutylammonium acetate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; 6.1: Rubottom oxidation / 15.1: Heck reaction / 18.1: Dess-Martin oxidation / 19.1: oxy-Michael reaction;
DOI:10.1021/ol201327u

Reference yield:

: 1311174-79-4
(1S,3aS,4S,7aS)-4-{2-[(1S,2S,6S)-1-(hydroxymethyl)-2-(methoxymethoxy)-7-oxabicyclo[4.1.0]heptan-2-yl]ethyl}-1-(methoxymethoxy)-7a-methylhexahydro-1H-inden-5(6H)-one

: 1311175-05-9
(3S,3aS,5R,5aR,7S,10aS,12aS,12bR)-7-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,5,5a,7,8,9,10,11,12,12b-tetradecahydro-10a,12a-epoxybenzo[4,5]cyclohepta-[1,2-e]inden-5-ol

Guidance literature:: Multi-step reaction with 19 steps

1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

2.1: zinc / methanol / 8 h / 20 °C / Inert atmosphere

3.1: 1H-imidazole; dmap / dichloromethane / 8 h / 20 °C / Inert atmosphere

4.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1.08 h / -78 - 20 °C / Inert atmosphere

4.2: 1.5 h / Inert atmosphere

5.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h / -20 °C / Inert atmosphere

6.1: formic acid / tetrahydrofuran; water / 2 h / 0 °C / Inert atmosphere

7.1: copper diacetate / methanol / 18 h / 20 °C / Inert atmosphere

8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 0 °C / Inert atmosphere

9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

10.1: diisobutylaluminium hydride / hexane; dichloromethane / 1.5 h / -78 °C / Inert atmosphere

11.1: pyridine; dmap / dichloromethane / 12 h / 0 °C / Inert atmosphere

12.1: chloro-trimethyl-silane; tetrabutylammomium bromide / dichloromethane / 0.31 h / 0 - 20 °C / Inert atmosphere

13.1: 1H-imidazole; 1,1,1,3,3,3-hexamethyl-disilazane / dichloromethane / 18 h / 20 °C / Inert atmosphere

14.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,3-bis-(diphenylphosphino)propane; cesium acetate; tetrabutylammonium acetate / N,N-dimethyl-formamide / 4.5 h / 20 - 70 °C / Inert atmosphere

15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

16.1: diisobutylaluminium hydride / hexane; dichloromethane / 1.5 h / -78 °C / Inert atmosphere

17.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

18.1: camphor-10-sulfonic acid / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

19.1: methanol; sodium tetrahydroborate / 1 h / 0 °C / Inert atmosphere

With pyridine; 1H-imidazole; methanol; dmap; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; chloro-trimethyl-silane; formic acid; camphor-10-sulfonic acid; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; iodine; cesium acetate; copper diacetate; tetrabutylammonium acetate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; 5.1: Rubottom oxidation / 14.1: Heck reaction / 17.1: Dess-Martin oxidation / 18.1: oxy-Michael reaction;
DOI:10.1021/ol201327u