(3S,3aS,5S,7aR)-7-{2-[(1S,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylene-1-(trimethylsilyloxy)cyclohexyl]ethyl}-3-(methoxymethoxy)-3a-methyl-6-(trifluoromethylsulfonyloxy)-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl acetate

Base Information

• Chemical Name: (3S,3aS,5S,7aR)-7-{2-[(1S,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylene-1-(trimethylsilyloxy)cyclohexyl]ethyl}-3-(methoxymethoxy)-3a-methyl-6-(trifluoromethylsulfonyloxy)-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl acetate
• CAS No.: 1311174-86-3
• Molecular Formula: C₄₃H₆₁F₃O₉SSi₂
• Molecular Weight: 867.184

Synonyms:(3S,3aS,5S,7aR)-7-{2-[(1S,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylene-1-(trimethylsilyloxy)cyclohexyl]ethyl}-3-(methoxymethoxy)-3a-methyl-6-(trifluoromethylsulfonyloxy)-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl acetate

Chemical Property of (3S,3aS,5S,7aR)-7-{2-[(1S,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylene-1-(trimethylsilyloxy)cyclohexyl]ethyl}-3-(methoxymethoxy)-3a-methyl-6-(trifluoromethylsulfonyloxy)-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (3S,3aS,5S,7aR)-7-{2-[(1S,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylene-1-(trimethylsilyloxy)cyclohexyl]ethyl}-3-(methoxymethoxy)-3a-methyl-6-(trifluoromethylsulfonyloxy)-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl acetate

There total 15 articles about (3S,3aS,5S,7aR)-7-{2-[(1S,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylene-1-(trimethylsilyloxy)cyclohexyl]ethyl}-3-(methoxymethoxy)-3a-methyl-6-(trifluoromethylsulfonyloxy)-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl acetate 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: 97.0%

chloro-trimethyl-silane (75-77-4) + (3S,3aS,5S,7aR)-7-{2-[(1S,3S)-3-(tert-butyldiphenylsilyloxy)-1-hydroxy-2-methylenecyclohexyl]ethyl}-3-(methoxymethoxy)-3a-methyl-6-(trifluoromethylsulfonyloxy)-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl acetate (1311175-00-4) → (3S,3aS,5S,7aR)-7-{2-[(1S,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylene-1-(trimethylsilyloxy)cyclohexyl]ethyl}-3-(methoxymethoxy)-3a-methyl-6-(trifluoromethylsulfonyloxy)-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl acetate (1311174-86-3)

Guidance literature:

With 1H-imidazole; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/ol201327u

Reference yield:

C35H64O7Si2 → (3S,3aS,5S,7aR)-7-{2-[(1S,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylene-1-(trimethylsilyloxy)cyclohexyl]ethyl}-3-(methoxymethoxy)-3a-methyl-6-(trifluoromethylsulfonyloxy)-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl acetate (1311174-86-3)

Guidance literature:

Multi-step reaction with 15 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

With pyridine; 1H-imidazole; dmap; n-butyllithium; chloro-trimethyl-silane; formic acid; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; iodine; copper diacetate; diisobutylaluminium hydride; sodium hydrogencarbonate; 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; 7.1: Rubottom oxidation;

DOI:10.1021/ol201327u

Reference yield:

C35H66O7Si2 (1311174-78-3) → (3S,3aS,5S,7aR)-7-{2-[(1S,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylene-1-(trimethylsilyloxy)cyclohexyl]ethyl}-3-(methoxymethoxy)-3a-methyl-6-(trifluoromethylsulfonyloxy)-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl acetate (1311174-86-3)

Guidance literature:

Multi-step reaction with 14 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

With pyridine; 1H-imidazole; dmap; n-butyllithium; chloro-trimethyl-silane; formic acid; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; iodine; copper diacetate; diisobutylaluminium hydride; sodium hydrogencarbonate; 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; 6.1: Rubottom oxidation;

DOI:10.1021/ol201327u

upstream raw materials:

chloro-trimethyl-silane

(3S,3aS,5S,7aR)-7-{2-[(1S,3S)-3-(tert-butyldiphenylsilyloxy)-1-hydroxy-2-methylenecyclohexyl]ethyl}-3-(methoxymethoxy)-3a-methyl-6-(trifluoromethylsulfonyloxy)-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl acetate

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

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,5S,7S,10aS,12bS)-7-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-3a-methyl-10a-(trimethylsilyloxy)-1,2,3,3a,4,5,7,8,9,10,10a,11,12,12b-tetradecahydrobenzo[4,5]cyclohepta[1,2-e]inden-5-yl acetate

(3S,3aS,5S,7S,10aS,12bS)-7-(tert-butyldiphenylsilyloxy)-10a-hydroxy-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,5,7,8,9,10,10a,11,12,12b-tetradecahydrobenzo[4,5]cyclohepta[1,2-e]inden-5-yl acetate

(3S,3aS,5S,7S,10aS,12bS)-7-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,5,7,8,9,10,10a,11,12,12b-tetradecahydrobenzo[4,5]cyclohepta[1,2-e]indene-5,10a-diol

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