(1R,3S,4S,5S,6R)-3-[(E)-1,5-dimethylhex-1-enyl]-4-methoxy-5-p-methoxybenzyloxy-7-oxabicyclo[4.1.0]heptan-2-one

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Chemical Name:(1R,3S,4S,5S,6R)-3-[(E)-1,5-dimethylhex-1-enyl]-4-methoxy-5-p-methoxybenzyloxy-7-oxabicyclo[4.1.0]heptan-2-one
CAS No.:527755-39-1
Molecular Formula:C₂₃H₃₂O₅
Molecular Weight:388.504
Hs Code.:

Synonyms:(1R,3S,4S,5S,6R)-3-[(E)-1,5-dimethylhex-1-enyl]-4-methoxy-5-p-methoxybenzyloxy-7-oxabicyclo[4.1.0]heptan-2-one

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Chemical Property of (1R,3S,4S,5S,6R)-3-[(E)-1,5-dimethylhex-1-enyl]-4-methoxy-5-p-methoxybenzyloxy-7-oxabicyclo[4.1.0]heptan-2-one

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Technology Process of (1R,3S,4S,5S,6R)-3-[(E)-1,5-dimethylhex-1-enyl]-4-methoxy-5-p-methoxybenzyloxy-7-oxabicyclo[4.1.0]heptan-2-one

There total 16 articles about (1R,3S,4S,5S,6R)-3-[(E)-1,5-dimethylhex-1-enyl]-4-methoxy-5-p-methoxybenzyloxy-7-oxabicyclo[4.1.0]heptan-2-one 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: 82.0%

: 527754-96-7
(4R,5S,6S)-5-methoxy-4-p-methoxybenzyloxy-6-[(E)-1,5-dimethylhex-1-enyl]cyclohex-2-enone

: 527755-39-1
(1R,3S,4S,5S,6R)-3-[(E)-1,5-dimethylhex-1-enyl]-4-methoxy-5-p-methoxybenzyloxy-7-oxabicyclo[4.1.0]heptan-2-one

Guidance literature:: With dihydrogen peroxide; potassium carbonate; In methanol; water; at 0 ℃; for 2h;
DOI:10.1021/jo035065+

Reference yield:

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

: 527755-39-1
(1R,3S,4S,5S,6R)-3-[(E)-1,5-dimethylhex-1-enyl]-4-methoxy-5-p-methoxybenzyloxy-7-oxabicyclo[4.1.0]heptan-2-one

Guidance literature:: Multi-step reaction with 10 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

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

Reference yield:

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

: 527755-39-1
(1R,3S,4S,5S,6R)-3-[(E)-1,5-dimethylhex-1-enyl]-4-methoxy-5-p-methoxybenzyloxy-7-oxabicyclo[4.1.0]heptan-2-one

Guidance literature:: Multi-step reaction with 9 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

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