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

Base Information

• Chemical Name: (3S,3aS,5aS,7S,10aS,12aS,12bR)-7-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,7,8,9,10,11,12,12b-dodecahydro-10a,12a-epoxybenzo[4,5]cyclohepta[1,2-e]inden-5(5aH)-one
• CAS No.: 1311174-91-0
• Molecular Formula: C₃₇H₄₈O₅Si
• Molecular Weight: 600.871

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 20 articles about (3S,3aS,5aS,7S,10aS,12aS,12bR)-7-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,7,8,9,10,11,12,12b-dodecahydro-10a,12a-epoxybenzo[4,5]cyclohepta[1,2-e]inden-5(5aH)-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: 60.0%

(3S,3aS,7S,10aS,12bS)-7-(tert-butyldiphenylsilyloxy)-10a-hydroxy-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,8,9,10,10a,11,12,12b-dodecahydrobenzo[4,5]cyclohepta[1,2-e]inden-5(7H)-one (1311174-90-9) → (3S,3aS,5aS,7S,10aS,12aS,12bR)-7-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,7,8,9,10,11,12,12b-dodecahydro-10a,12a-epoxybenzo[4,5]cyclohepta[1,2-e]inden-5(5aH)-one (1311174-91-0)

Guidance literature:

With camphor-10-sulfonic acid; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ol201327u

Reference yield:

C35H64O7Si2 → (3S,3aS,5aS,7S,10aS,12aS,12bR)-7-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,7,8,9,10,11,12,12b-dodecahydro-10a,12a-epoxybenzo[4,5]cyclohepta[1,2-e]inden-5(5aH)-one (1311174-91-0)

Guidance literature:

Multi-step reaction with 20 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

With pyridine; 1H-imidazole; dmap; 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:

C35H66O7Si2 (1311174-78-3) → (3S,3aS,5aS,7S,10aS,12aS,12bR)-7-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,7,8,9,10,11,12,12b-dodecahydro-10a,12a-epoxybenzo[4,5]cyclohepta[1,2-e]inden-5(5aH)-one (1311174-91-0)

Guidance literature:

Multi-step reaction with 19 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

With pyridine; 1H-imidazole; dmap; 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

upstream raw materials:

C₃₅H₆₆O₇Si₂

(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

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

(1S,3aS,4R,7aS)-4-{2-[(1S,3S)-3-hydroxy-1-(methoxymethoxy)-2-methylenecyclohexyl]ethyl}-1-(methoxymethoxy)-7a-methylhexahydro-1H-inden-5(6H)-one

Downstream raw materials:

tert-butyl {(3S,3aS,7S,10aS,12aS,12bR)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,7,8,9,10,11,12,12b-dodecahydro-10a,12a-epoxybenzo[4,5]cyclohepta[1,2-e]inden-7-yl}oxydiphenylsilane

(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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