(4R,5S,6S)-4-p-methoxybenzyloxy-5-trimethylsilyloxy-6-[(E)-1,5-dimethyl-hex-1,4-dienyl]-cyclohex-2-enone

Base Information

Chemical Name:(4R,5S,6S)-4-p-methoxybenzyloxy-5-trimethylsilyloxy-6-[(E)-1,5-dimethyl-hex-1,4-dienyl]-cyclohex-2-enone
CAS No.:364337-25-7
Molecular Formula:C₂₅H₃₆O₄Si
Molecular Weight:428.644
Hs Code.:

Synonyms:(4R,5S,6S)-4-p-methoxybenzyloxy-5-trimethylsilyloxy-6-[(E)-1,5-dimethyl-hex-1,4-dienyl]-cyclohex-2-enone

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Chemical Property of (4R,5S,6S)-4-p-methoxybenzyloxy-5-trimethylsilyloxy-6-[(E)-1,5-dimethyl-hex-1,4-dienyl]-cyclohex-2-enone

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Technology Process of (4R,5S,6S)-4-p-methoxybenzyloxy-5-trimethylsilyloxy-6-[(E)-1,5-dimethyl-hex-1,4-dienyl]-cyclohex-2-enone

There total 12 articles about (4R,5S,6S)-4-p-methoxybenzyloxy-5-trimethylsilyloxy-6-[(E)-1,5-dimethyl-hex-1,4-dienyl]-cyclohex-2-enone 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: 53.0%

: 364337-24-6
(4S,5E)-4-[(1S,2R)-2-p-methoxybenzyloxy-1-trimethylsilyloxy-but-3-enyl]-5,9-dimethyl-deca-1,5,8-trienone

: 364337-25-7
(4R,5S,6S)-4-p-methoxybenzyloxy-5-trimethylsilyloxy-6-[(E)-1,5-dimethyl-hex-1,4-dienyl]-cyclohex-2-enone

Guidance literature:: (4S,5E)-4-[(1S,2R)-2-p-methoxybenzyloxy-1-trimethylsilyloxy-but-3-enyl]-5,9-dimethyl-deca-1,5,8-trienone; With titanium(IV) isopropylate; In dichloromethane; at 30 ℃; for 0.5h;

Grubbs catalyst first generation; In dichloromethane; at 55 ℃; for 24h; Further stages.;
DOI:10.1021/ol016343z

Reference yield:

: 16750-94-0
2,6-dimethyl-2,5-octadien-8-ol

: 364337-25-7
(4R,5S,6S)-4-p-methoxybenzyloxy-5-trimethylsilyloxy-6-[(E)-1,5-dimethyl-hex-1,4-dienyl]-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 9 steps

1.1: 35 percent / CrO₃; sulfuric acid / H₂O; acetone / 0.25 h / 0 °C

2.1: triethylamine / tetrahydrofuran / 0.5 h / -78 - 0 °C

3.1: 188 mg / tetrahydrofuran; hexane / 0.33 h / -78 °C

4.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C

4.2: tetrahydrofuran; hexane / 0.75 h / -78 °C

5.1: 4.61 g / tetrabutylammonium periodate / CHCl₃ / 2 h / 60 °C

6.1: trimethylaluminium / toluene; tetrahydrofuran / 0.75 h / 20 °C

6.2: 71 percent / toluene; tetrahydrofuran / 0 °C

7.1: 100 percent / triethylamine; DMAP / tetrahydrofuran / 2 h / 20 °C

8.1: 87 percent / tetrahydrofuran / 12 h / 20 °C

9.1: Ti(O-i-Pr)4 / CH₂Cl₂ / 0.5 h / 30 °C

9.2: 53 percent / Grubb's complex "type 1" / CH₂Cl₂ / 24 h / 55 °C

With chromium(VI) oxide; titanium(IV) isopropylate; dmap; sulfuric acid; trimethylaluminum; tetrabutylammonium periodite; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; chloroform; water; acetone; toluene;
DOI:10.1021/ol016343z

Reference yield:

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

: 364337-25-7
(4R,5S,6S)-4-p-methoxybenzyloxy-5-trimethylsilyloxy-6-[(E)-1,5-dimethyl-hex-1,4-dienyl]-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 8 steps

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

2.1: 94 percent / DIBAH / toluene / 0.33 h / -78 °C

3.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C

3.2: tetrahydrofuran; hexane / 0.75 h / -78 °C

4.1: 4.61 g / tetrabutylammonium periodate / CHCl₃ / 2 h / 60 °C

5.1: trimethylaluminium / toluene; tetrahydrofuran / 0.75 h / 20 °C

5.2: 71 percent / toluene; tetrahydrofuran / 0 °C

6.1: 100 percent / triethylamine; DMAP / tetrahydrofuran / 2 h / 20 °C

7.1: 87 percent / tetrahydrofuran / 12 h / 20 °C

8.1: Ti(O-i-Pr)4 / CH₂Cl₂ / 0.5 h / 30 °C

8.2: 53 percent / Grubb's complex "type 1" / CH₂Cl₂ / 24 h / 55 °C

With titanium(IV) isopropylate; dmap; camphor-10-sulfonic acid; trimethylaluminum; diisobutylaluminium hydride; tetrabutylammonium periodite; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; chloroform; toluene;
DOI:10.1021/ol016343z