3-[(1R,3aR,4S,7aR)-4-(tert-butyldimethylsilanyloxy)-7a-methyloctahydroinden-1-yl]but-3-enyl tolene-4-sulfonate

Base Information

Chemical Name:3-[(1R,3aR,4S,7aR)-4-(tert-butyldimethylsilanyloxy)-7a-methyloctahydroinden-1-yl]but-3-enyl tolene-4-sulfonate
CAS No.:713522-38-4
Molecular Formula:C₂₇H₄₄O₄SSi
Molecular Weight:492.795
Hs Code.:

Synonyms:3-[(1R,3aR,4S,7aR)-4-(tert-butyldimethylsilanyloxy)-7a-methyloctahydroinden-1-yl]but-3-enyl tolene-4-sulfonate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 3-[(1R,3aR,4S,7aR)-4-(tert-butyldimethylsilanyloxy)-7a-methyloctahydroinden-1-yl]but-3-enyl tolene-4-sulfonate

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of 3-[(1R,3aR,4S,7aR)-4-(tert-butyldimethylsilanyloxy)-7a-methyloctahydroinden-1-yl]but-3-enyl tolene-4-sulfonate

There total 1 articles about 3-[(1R,3aR,4S,7aR)-4-(tert-butyldimethylsilanyloxy)-7a-methyloctahydroinden-1-yl]but-3-enyl tolene-4-sulfonate 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: 99.0%

: 98-59-9
p-toluenesulfonyl chloride

: 221046-11-3
[1R-(1α, 3aβ,4α,7aα)]-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]octahydro-7a-methyl-γ-methylene-1H-indene-1-propanol

: 713522-38-4
3-[(1R,3aR,4S,7aR)-4-(tert-butyldimethylsilanyloxy)-7a-methyloctahydroinden-1-yl]but-3-enyl tolene-4-sulfonate

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 5h;
DOI:10.1002/ejoc.200300718

Reference yield:

: 713522-38-4
3-[(1R,3aR,4S,7aR)-4-(tert-butyldimethylsilanyloxy)-7a-methyloctahydroinden-1-yl]but-3-enyl tolene-4-sulfonate

: (1R,3S)-5-{2-[(1R,3aS,7aR)-7a-methyl-1-[(S)-6,6,6-trifluoro-5-hydroxy-1-(4-hydroxy-4-methylpentyl)-5-(trifluoromethyl)hex-3-ynyl]octahydroinden-(4E)-ylidene]ethylidene}-4-methylenecyclohexane-1,3-diol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 91 percent / sodium hydride / toluene / 5 h / 120 °C

2.1: 87 percent / lithium chloride; aq. DMSO / 3 h / 160 °C

3.1: 88 percent / diethyl ether / 3 h / 20 °C

4.1: borane*THF / tetrahydrofuran / 20 °C

4.2: 1.3114 g / aq. sodium percarbonate / 1.17 h / Heating

5.1: 98 percent / triphenylphosphane; imidazole; iodine / CH₂Cl₂ / 0.67 h / cooling

6.1: dimethylsulfoxide; tetrahydrofuran

7.1: 93 percent / cyclohexane / 4 h

8.1: butyllithium / tetrahydrofuran; hexane / 0.13 h / cooling

8.2: tetrahydrofuran; hexane / 0.08 h / cooling

9.1: fluorosilicic acid / acetonitrile / 4 h / cooling

10.1: 88 percent / pyridinium dichromate; Celite / CH₂Cl₂; diethyl ether / 6 h

11.1: 0.30 g / diethyl ether / 1 h

12.1: butyllithium / tetrahydrofuran; hexane / 0.17 h / -75 °C

12.2: tetrahydrofuran; hexane / 4.5 h / -75 °C

12.3: 78 percent / tetrabutylammonium fluoride / ethyl acetate / 24 h / 20 °C

With 1H-imidazole; dipyridinium dichromate; n-butyllithium; fluorosilicic acid; borane-THF; Celite; iodine; sodium hydride; dimethyl sulfoxide; triphenylphosphine; lithium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; dimethyl sulfoxide; toluene; acetonitrile;
DOI:10.1002/ejoc.200300718

Reference yield:

: 713522-38-4
3-[(1R,3aR,4S,7aR)-4-(tert-butyldimethylsilanyloxy)-7a-methyloctahydroinden-1-yl]but-3-enyl tolene-4-sulfonate

: (S)-6-{(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-1,1,1-trifluoro-10-methyl-2-trifluoromethyl-10-trimethylsilanyloxy-undec-3-yn-2-ol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 91 percent / sodium hydride / toluene / 5 h / 120 °C

2.1: 87 percent / lithium chloride; aq. DMSO / 3 h / 160 °C

3.1: 88 percent / diethyl ether / 3 h / 20 °C

4.1: borane*THF / tetrahydrofuran / 20 °C

4.2: 1.3114 g / aq. sodium percarbonate / 1.17 h / Heating

5.1: 98 percent / triphenylphosphane; imidazole; iodine / CH₂Cl₂ / 0.67 h / cooling

6.1: dimethylsulfoxide; tetrahydrofuran

7.1: 93 percent / cyclohexane / 4 h

8.1: butyllithium / tetrahydrofuran; hexane / 0.13 h / cooling

8.2: tetrahydrofuran; hexane / 0.08 h / cooling

9.1: fluorosilicic acid / acetonitrile / 4 h / cooling

10.1: 88 percent / pyridinium dichromate; Celite / CH₂Cl₂; diethyl ether / 6 h

11.1: 0.30 g / diethyl ether / 1 h

12.1: butyllithium / tetrahydrofuran; hexane / -75 °C

12.2: tetrahydrofuran; hexane / -75 °C

With 1H-imidazole; dipyridinium dichromate; n-butyllithium; fluorosilicic acid; borane-THF; Celite; iodine; sodium hydride; dimethyl sulfoxide; triphenylphosphine; lithium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; dimethyl sulfoxide; toluene; acetonitrile;
DOI:10.1002/ejoc.200300718