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

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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}ethanol
CAS No.:934968-41-9
Molecular Formula:C₂₇H₄₂O₂Si
Molecular Weight:426.715
Hs Code.:

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}ethanol

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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}ethanol

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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}ethanol

There total 7 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}ethanol 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: 88.0%

: 934968-38-4
(1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl-2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl} acetate

: 934968-41-9
2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}ethanol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 2h;
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

: 934968-41-9
2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}ethanol

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; (PhSeO)2O; diisobutylaluminium hydride; toluene-4-sulfonic acid; cyclohexene; In tetrahydrofuran; ethanol; hexane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1002/chem.200600728

Reference yield:

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

: 934968-41-9
2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}ethanol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 606 mg / NaBH₄ / ethanol / 1.5 h / 0 °C

2.1: 94 percent / TsOH / acetone; H₂O / 48 h / 20 °C

3.1: 93 percent / imidazole / dimethylformamide / 16 h / 20 °C

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

4.2: 79 percent / tetrahydrofuran / 168 h / -62 °C

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

5.2: 82 percent / aq. NaHCO₃; aq. NH₄Cl / tetrahydrofuran; diethyl ether; hexane

6.1: 88 percent / diisobutylaluminum hydride / tetrahydrofuran / 2 h / 0 - 20 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; ethanol; hexane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1002/chem.200600728