(2R)-2,3-Dihydro-5-methoxy-3β-methyl-7-(2-propenyl)-2α-(3,4,5-trimethoxyphenyl)-1,4-benzodioxin

Base Information

• Chemical Name: (2R)-2,3-Dihydro-5-methoxy-3β-methyl-7-(2-propenyl)-2α-(3,4,5-trimethoxyphenyl)-1,4-benzodioxin
• CAS No.: 59332-00-2
• Molecular Formula: C₂₂H₂₆O₆
• Molecular Weight: 386.445
• Mol file: 59332-00-2.mol

Synonyms:eusiderin-A;eusiderin;(2R,3R)-7-Allyl-5-methoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-2,3-dihydro-benzo[1,4]dioxine;(?)-eusiderin A;

Chemical Property of (2R)-2,3-Dihydro-5-methoxy-3β-methyl-7-(2-propenyl)-2α-(3,4,5-trimethoxyphenyl)-1,4-benzodioxin

Chemical Property:

• PSA: 55.38000
• LogP: 4.35050

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R)-2,3-Dihydro-5-methoxy-3β-methyl-7-(2-propenyl)-2α-(3,4,5-trimethoxyphenyl)-1,4-benzodioxin

There total 3 articles about (2R)-2,3-Dihydro-5-methoxy-3β-methyl-7-(2-propenyl)-2α-(3,4,5-trimethoxyphenyl)-1,4-benzodioxin 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:

(2R)-2-(4'-bromo-2'-hydroxy-6'-methoxyphenoxy)-1-(3',4',5'-trimethoxyphenyl)propan-1-ol → eusidérine A (59332-00-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Amberlyst 15 / toluene / 21 h / Inert atmosphere; Reflux

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride / tetrahydrofuran / 18 h / Inert atmosphere; Reflux

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride; In tetrahydrofuran; toluene; 2: |Suzuki Coupling;

DOI:10.1021/jo3015006

Reference yield:

(2R)-2-(4'-bromo-2'-hydroxy-6'-methoxyphenoxy)-1-(3',4',5'-trimethoxyphenyl)propan-1-ol → (2R,3R)-3-methyl-2-(3',4',5'-trimethoxyphenyl)-5-methoxy-1,4-benzodioxane (1395922-49-2) + eusidérine A (59332-00-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Amberlyst 15 / toluene / 21 h / Inert atmosphere; Reflux

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride / tetrahydrofuran / 24 h / Inert atmosphere; Reflux

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride; In tetrahydrofuran; toluene; 2: |Suzuki Coupling;

DOI:10.1021/jo3015006

Reference yield:

(2R,3R)-3-methyl-2-(3',4',5'-trimethoxyphenyl)-7-bromo-5-methoxy-1,4-benzodioxane (1395922-48-1) + 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) → (2R,3R)-3-methyl-2-(3',4',5'-trimethoxyphenyl)-5-methoxy-1,4-benzodioxane (1395922-49-2) + eusidérine A (59332-00-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride; In tetrahydrofuran; for 24h; Inert atmosphere; Reflux;

DOI:10.1021/jo3015006

upstream raw materials:

(2R,3R)-3-methyl-2-(3',4',5'-trimethoxyphenyl)-7-bromo-5-methoxy-1,4-benzodioxane

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Refernces