2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}ethyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: 2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}ethyl 4-methylbenzenesulfonate
• CAS No.: 934968-45-3
• Molecular Formula: C₃₄H₄₈O₄SSi
• Molecular Weight: 580.904

Synonyms:2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}ethyl 4-methylbenzenesulfonate

Chemical Property of 2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}ethyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}ethyl 4-methylbenzenesulfonate

There total 8 articles about 2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}ethyl 4-methylbenzenesulfonate 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: 90.0%

2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}ethanol (934968-41-9) + p-toluenesulfonyl chloride (98-59-9) → 2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}ethyl 4-methylbenzenesulfonate (934968-45-3)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; triethylamine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1002/chem.200600728

Reference yield:

(3a'S,4'R,5'R,6a'R)-5,5-dimethyl-4'-[(E)-4-m-tolylbut-1-enyl]hexahydro-1'H-spiro([1,3]dioxane-2,2'-pentalen)-5'-ol (934968-25-9) → 2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}ethyl 4-methylbenzenesulfonate (934968-45-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 94 percent / TsOH / acetone; H₂O / 48 h / 20 °C

2.1: 93 percent / imidazole / dimethylformamide / 16 h / 20 °C

3.1: nBuLi / tetrahydrofuran / -62 - 20 °C

3.2: 79 percent / tetrahydrofuran / 168 h / -62 °C

4.1: nBuLi; bis[(R)-1-phenylethyl]ammonium chloride / tetrahydrofuran; hexane / 1.5 h / -78 °C

4.2: 82 percent / aq. NaHCO₃; aq. NH₄Cl / tetrahydrofuran; diethyl ether; hexane

5.1: 88 percent / diisobutylaluminum hydride / tetrahydrofuran / 2 h / 0 - 20 °C

6.1: 90 percent / NEt₃; 1,4-diazabicyclo[2.2.2]octane / CH₂Cl₂ / 12 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; n-butyllithium; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1002/chem.200600728

Reference yield:

(E)-N'-{(3a'S,4'R,6a'R)-5,5-dimethyl-4'-[(E)-4-m-tolylbut-1-enyl]dihydro-1'H-spiro([1,3]dioxane-2,2'-pentalene)-5'-(3'H,6'H,6a'H)ylidene}-4-methylbenzenesulfonohydrazide → 2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}ethyl 4-methylbenzenesulfonate (934968-45-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: (PhSeO)2O; cyclohexene / tetrahydrofuran / 0.75 h / 20 °C

2.1: 606 mg / NaBH₄ / ethanol / 1.5 h / 0 °C

3.1: 94 percent / TsOH / acetone; H₂O / 48 h / 20 °C

4.1: 93 percent / imidazole / dimethylformamide / 16 h / 20 °C

5.1: nBuLi / tetrahydrofuran / -62 - 20 °C

5.2: 79 percent / tetrahydrofuran / 168 h / -62 °C

6.1: nBuLi; bis[(R)-1-phenylethyl]ammonium chloride / tetrahydrofuran; hexane / 1.5 h / -78 °C

6.2: 82 percent / aq. NaHCO₃; aq. NH₄Cl / tetrahydrofuran; diethyl ether; hexane

7.1: 88 percent / diisobutylaluminum hydride / tetrahydrofuran / 2 h / 0 - 20 °C

8.1: 90 percent / NEt₃; 1,4-diazabicyclo[2.2.2]octane / CH₂Cl₂ / 12 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; sodium tetrahydroborate; n-butyllithium; (PhSeO)2O; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; cyclohexene; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1002/chem.200600728

upstream raw materials:

2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}ethanol

p-toluenesulfonyl chloride

(3a'S,4'R,5'R,6a'R)-5,5-dimethyl-4'-[(E)-4-m-tolylbut-1-enyl]hexahydro-1'H-spiro([1,3]dioxane-2,2'-pentalen)-5'-ol

(3aS,4R,5R,6aR)-5-hydroxy-4-[(E)-4-m-tolylbut-1-enyl]hexahydropentalen-2(1H)-one

Downstream raw materials:

tert-butyldimethyl{(2R,3R,3aS,6aS)-5-[5-(tetrahydro-2H-pyran-2-yloxy)pentyl]-3-[(E)-4-m-tolylbut-1-enyl]-1,2,3,3a,4,6a-hexahydropentalen-2-yloxy}silane

5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentan-1-ol

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