(2S,3S,4S,5S)-2-[(E)-1,5-dimethylhex-1-enyl]-5-(isopropyldimethylsilanyloxy)-3-methoxy-4-p-methoxybenzyloxycyclohexanone

Base Information

Chemical Name:(2S,3S,4S,5S)-2-[(E)-1,5-dimethylhex-1-enyl]-5-(isopropyldimethylsilanyloxy)-3-methoxy-4-p-methoxybenzyloxycyclohexanone
CAS No.:527755-43-7
Molecular Formula:C₂₈H₄₆O₅Si
Molecular Weight:490.756
Hs Code.:

Synonyms:(2S,3S,4S,5S)-2-[(E)-1,5-dimethylhex-1-enyl]-5-(isopropyldimethylsilanyloxy)-3-methoxy-4-p-methoxybenzyloxycyclohexanone

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Chemical Property of (2S,3S,4S,5S)-2-[(E)-1,5-dimethylhex-1-enyl]-5-(isopropyldimethylsilanyloxy)-3-methoxy-4-p-methoxybenzyloxycyclohexanone

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Technology Process of (2S,3S,4S,5S)-2-[(E)-1,5-dimethylhex-1-enyl]-5-(isopropyldimethylsilanyloxy)-3-methoxy-4-p-methoxybenzyloxycyclohexanone

There total 18 articles about (2S,3S,4S,5S)-2-[(E)-1,5-dimethylhex-1-enyl]-5-(isopropyldimethylsilanyloxy)-3-methoxy-4-p-methoxybenzyloxycyclohexanone 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: 76.0%

: 3634-56-8
isopropyldimethylsilyl chloride

: 527755-41-5
(2S,3S,4R,5S)-2-[(E)-1,5-dimethylhex-1-enyl]-5-hydroxy-3-methoxy-4-p-methoxybenzyloxycyclohexanone

: 527755-43-7
(2S,3S,4S,5S)-2-[(E)-1,5-dimethylhex-1-enyl]-5-(isopropyldimethylsilanyloxy)-3-methoxy-4-p-methoxybenzyloxycyclohexanone

Guidance literature:: With dmap; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1021/jo035065+

Reference yield:

: 56134-54-4
(E)-3,7-dimethyloct-3-enol

: 527755-43-7
(2S,3S,4S,5S)-2-[(E)-1,5-dimethylhex-1-enyl]-5-(isopropyldimethylsilanyloxy)-3-methoxy-4-p-methoxybenzyloxycyclohexanone

Guidance literature:: Multi-step reaction with 12 steps

1.1: 65 percent / CrO₃; H₂SO₄ / H₂O; acetone / 0.25 h / 0 °C

2.1: oxalyl chloride; DMF / CH₂Cl₂ / 4 h / 0 - 20 °C

3.1: 9.16 g / BuLi / tetrahydrofuran; hexane / -78 - 0 °C

4.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 55 percent / tetrahydrofuran; hexane / 1 h / -78 °C

5.1: 5.83 g / tetrabutylammonium periodate / CHCl₃ / 2 h / 60 °C

6.1: trimethylaluminum / toluene; tetrahydrofuran / 0.5 h / 20 °C

6.2: 75 percent / toluene; tetrahydrofuran / 24 h / 20 °C

7.1: 93 percent / Ag₂O / diethyl ether / 8 h / 45 °C

8.1: 86 percent / tetrahydrofuran / 12 h / 20 °C

9.1: 78 percent / [(1,3-dimesitylimidazolidin-2-yl){P(c-hexyl)3}RuCl₂(=CHPh)] / toluene / 0.75 h / 70 °C

10.1: 82 percent / H₂O₂; K₂CO₃ / methanol; H₂O / 2 h / 0 °C

11.1: 82 percent / NaBH₄; diphenyl diselenide; acetic acid / ethanol / 0.25 h / 0 °C

12.1: 76 percent / 4-(dimethylamino)pyridine / tetrahydrofuran; dimethylformamide / 1 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; chromium(VI) oxide; dmap; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; sulfuric acid; diphenyl diselenide; dihydrogen peroxide; trimethylaluminum; potassium carbonate; tetrabutylammonium periodite; acetic acid; N,N-dimethyl-formamide; silver(l) oxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/jo035065+

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 527755-43-7
(2S,3S,4S,5S)-2-[(E)-1,5-dimethylhex-1-enyl]-5-(isopropyldimethylsilanyloxy)-3-methoxy-4-p-methoxybenzyloxycyclohexanone

Guidance literature:: Multi-step reaction with 11 steps

1.1: 70 percent / camphorsulfonic acid / CH₂Cl₂ / 24 h / 20 °C

2.1: DIBAL-H / toluene / 0.33 h / -78 °C

3.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 55 percent / tetrahydrofuran; hexane / 1 h / -78 °C

4.1: 5.83 g / tetrabutylammonium periodate / CHCl₃ / 2 h / 60 °C

5.1: trimethylaluminum / toluene; tetrahydrofuran / 0.5 h / 20 °C

5.2: 75 percent / toluene; tetrahydrofuran / 24 h / 20 °C

6.1: 93 percent / Ag₂O / diethyl ether / 8 h / 45 °C

7.1: 86 percent / tetrahydrofuran / 12 h / 20 °C

8.1: 78 percent / [(1,3-dimesitylimidazolidin-2-yl){P(c-hexyl)3}RuCl₂(=CHPh)] / toluene / 0.75 h / 70 °C

9.1: 82 percent / H₂O₂; K₂CO₃ / methanol; H₂O / 2 h / 0 °C

10.1: 82 percent / NaBH₄; diphenyl diselenide; acetic acid / ethanol / 0.25 h / 0 °C

11.1: 76 percent / 4-(dimethylamino)pyridine / tetrahydrofuran; dimethylformamide / 1 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium tetrahydroborate; diphenyl diselenide; camphor-10-sulfonic acid; dihydrogen peroxide; trimethylaluminum; diisobutylaluminium hydride; potassium carbonate; tetrabutylammonium periodite; acetic acid; silver(l) oxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo035065+