(-)-5-benzyloxy-2-chloro-6-[(2E,4E)-5-{(1R,2R,6R)-3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl}-3-methylpenta-2,4-dienyl]-3-methylphenol

Base Information

Chemical Name:(-)-5-benzyloxy-2-chloro-6-[(2E,4E)-5-{(1R,2R,6R)-3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl}-3-methylpenta-2,4-dienyl]-3-methylphenol
CAS No.:307492-55-3
Molecular Formula:C₃₁H₃₉ClO₄
Molecular Weight:511.101
Hs Code.:

Synonyms:(-)-5-benzyloxy-2-chloro-6-[(2E,4E)-5-{(1R,2R,6R)-3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl}-3-methylpenta-2,4-dienyl]-3-methylphenol

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Chemical Property of (-)-5-benzyloxy-2-chloro-6-[(2E,4E)-5-{(1R,2R,6R)-3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl}-3-methylpenta-2,4-dienyl]-3-methylphenol

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Technology Process of (-)-5-benzyloxy-2-chloro-6-[(2E,4E)-5-{(1R,2R,6R)-3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl}-3-methylpenta-2,4-dienyl]-3-methylphenol

There total 7 articles about (-)-5-benzyloxy-2-chloro-6-[(2E,4E)-5-{(1R,2R,6R)-3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl}-3-methylpenta-2,4-dienyl]-3-methylphenol 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: 65.0%

: 4-chloro-3-methylcyclobut-2-enone

: 307492-54-2
(-)-benzyl (4E,6E)-7-[(1R,2R,6R)-3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl]-5-methylhepta-4,6-dien-1-ynyl ether

: 307492-55-3
(-)-5-benzyloxy-2-chloro-6-[(2E,4E)-5-{(1R,2R,6R)-3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl}-3-methylpenta-2,4-dienyl]-3-methylphenol

Guidance literature:: 4-chloro-3-methylcyclobut-2-enone; (-)-benzyl (4E,6E)-7-[(1R,2R,6R)-3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl]-5-methylhepta-4,6-dien-1-ynyl ether; In benzene-d6; for 40h; Irradiation;

In toluene; for 4h; Further stages.; Heating;
DOI:10.1021/ol006561c

Reference yield:

: 2,3,4-trimethyl-3-[5'-t-butyldimethylsilyloxy-3'-methyl-(1E,3E)-pentadienyl]-cyclohexanone

: 307492-55-3
(-)-5-benzyloxy-2-chloro-6-[(2E,4E)-5-{(1R,2R,6R)-3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl}-3-methylpenta-2,4-dienyl]-3-methylphenol

Guidance literature:: Multi-step reaction with 5 steps

1.1: TBAF / dimethylformamide; tetrahydrofuran / 5 h / 0 °C

2.1: 76 percent / p-TsOH; CaSO₄ / cyclohexane / 3.5 h / 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

3.2: tetrahydrofuran; hexane / 1.5 h / -78 °C

4.1: 77 percent / Li₂CuCl₄ / tetrahydrofuran; hexane / 2.5 h / 0 °C

5.1: benzene-d6 / 40 h / Irradiation

5.2: 65 percent / toluene / 4 h / Heating

With calcium sulfate; n-butyllithium; dilithium tetrachlorocuprate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; cyclohexane; benzene-d6; N,N-dimethyl-formamide;
DOI:10.1021/ol006561c

Reference yield:

: 99529-50-7
(2E,4E,1'R,2'R,6'R)-(-)-5-(3',3'-ethylenedioxy-1',2',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadien-1-ol

: 307492-55-3
(-)-5-benzyloxy-2-chloro-6-[(2E,4E)-5-{(1R,2R,6R)-3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl}-3-methylpenta-2,4-dienyl]-3-methylphenol

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: tetrahydrofuran; hexane / 1.5 h / -78 °C

2.1: 77 percent / Li₂CuCl₄ / tetrahydrofuran; hexane / 2.5 h / 0 °C

3.1: benzene-d6 / 40 h / Irradiation

3.2: 65 percent / toluene / 4 h / Heating

With n-butyllithium; dilithium tetrachlorocuprate; In tetrahydrofuran; hexane; benzene-d6;
DOI:10.1021/ol006561c