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

Base Information

• Chemical Name: (2R,3R)-3-methyl-2-(3',4',5'-trimethoxyphenyl)-5-methoxy-1,4-benzodioxane
• CAS No.: 1395922-49-2
• Molecular Formula: C₁₉H₂₂O₆
• Molecular Weight: 346.38
• Mol file: 1395922-49-2.mol

Synonyms:(2R,3R)-3-methyl-2-(3',4',5'-trimethoxyphenyl)-5-methoxy-1,4-benzodioxane

Chemical Property of (2R,3R)-3-methyl-2-(3',4',5'-trimethoxyphenyl)-5-methoxy-1,4-benzodioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-methyl-2-(3',4',5'-trimethoxyphenyl)-5-methoxy-1,4-benzodioxane

There total 4 articles about (2R,3R)-3-methyl-2-(3',4',5'-trimethoxyphenyl)-5-methoxy-1,4-benzodioxane 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%

(2R,3R)-3-methyl-2-(3',4',5'-trimethoxyphenyl)-7-bromo-5-methoxy-1,4-benzodioxane (1395922-48-1) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → (2R,3R)-3-methyl-2-(3',4',5'-trimethoxyphenyl)-5-methoxy-1,4-benzodioxane (1395922-49-2) + (-)-eusiderin L

Guidance literature:

(2R,3R)-3-methyl-2-(3',4',5'-trimethoxyphenyl)-7-bromo-5-methoxy-1,4-benzodioxane; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; for 0.0833333h; Inert atmosphere;

N,N-dimethyl-formamide; In tetrahydrofuran; at -78 - 20 ℃; for 2h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; water;

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)

Guidance literature:

Multi-step reaction with 2 steps

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

2.1: tert.-butyl lithium / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 - 20 °C / Inert atmosphere

With tert.-butyl lithium; In tetrahydrofuran; toluene;

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

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

N,N-dimethyl-formamide

Refernces