5-[(E)-(5S,6R,8S)-8-Hydroxy-6-(4-methoxy-benzyloxy)-5-methyl-undeca-2,10-dienyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one

Base Information

Chemical Name:5-[(E)-(5S,6R,8S)-8-Hydroxy-6-(4-methoxy-benzyloxy)-5-methyl-undeca-2,10-dienyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one
CAS No.:507480-11-7
Molecular Formula:C₃₀H₃₈O₆
Molecular Weight:494.628
Hs Code.:

Synonyms:5-[(E)-(5S,6R,8S)-8-Hydroxy-6-(4-methoxy-benzyloxy)-5-methyl-undeca-2,10-dienyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one

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Chemical Property of 5-[(E)-(5S,6R,8S)-8-Hydroxy-6-(4-methoxy-benzyloxy)-5-methyl-undeca-2,10-dienyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one

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Technology Process of 5-[(E)-(5S,6R,8S)-8-Hydroxy-6-(4-methoxy-benzyloxy)-5-methyl-undeca-2,10-dienyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one

There total 3 articles about 5-[(E)-(5S,6R,8S)-8-Hydroxy-6-(4-methoxy-benzyloxy)-5-methyl-undeca-2,10-dienyl]-2,2-dimethyl-benzo[1,3]dioxin-4-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: 73.0%

: 507480-02-6
5-(bromomethyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

: (E)-(4S,6R,7S)-6-(4-Methoxy-benzyloxy)-7-methyl-10-tributylstannanyl-deca-1,9-dien-4-ol

: 507480-11-7
5-[(E)-(5S,6R,8S)-8-Hydroxy-6-(4-methoxy-benzyloxy)-5-methyl-undeca-2,10-dienyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one

Guidance literature:: With trifuran-2-yl-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 15h;
DOI:10.1021/jo026798h

Reference yield:

: 567-61-3
2-hydroxy-6-methylbenzoic acid

: 507480-11-7
5-[(E)-(5S,6R,8S)-8-Hydroxy-6-(4-methoxy-benzyloxy)-5-methyl-undeca-2,10-dienyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one

Guidance literature:: Multi-step reaction with 3 steps

1: 89 percent / DMAP; thionyl chloride / 1,2-dimethoxy-ethane / 3 h

2: 75 percent / N-bromosuccinimide; benzoyl peroxide / CCl₄ / 15 h / Heating

3: 73 percent / tri-2-furylphosphine / tris(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1-methyl-pyrrolidin-2-one / 15 h / 20 °C

With dmap; N-Bromosuccinimide; thionyl chloride; trifuran-2-yl-phosphane; dibenzoyl peroxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1-methyl-pyrrolidin-2-one; tetrachloromethane; 1,2-dimethoxyethane; 3: Stille coupling;
DOI:10.1021/jo026798h

Reference yield:

: 438187-08-7
2, 2, 5-trimethyl-4H-benzo[d][1,3]dioxin-4-one

: 507480-11-7
5-[(E)-(5S,6R,8S)-8-Hydroxy-6-(4-methoxy-benzyloxy)-5-methyl-undeca-2,10-dienyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one

Guidance literature:: Multi-step reaction with 2 steps

1: 75 percent / N-bromosuccinimide; benzoyl peroxide / CCl₄ / 15 h / Heating

2: 73 percent / tri-2-furylphosphine / tris(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1-methyl-pyrrolidin-2-one / 15 h / 20 °C

With N-Bromosuccinimide; trifuran-2-yl-phosphane; dibenzoyl peroxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1-methyl-pyrrolidin-2-one; tetrachloromethane; 2: Stille coupling;
DOI:10.1021/jo026798h