(1R,2R)-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)-1-(3,4,5-trimethoxyphenyl)propane-1,3-diol

Base Information

• Chemical Name: (1R,2R)-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)-1-(3,4,5-trimethoxyphenyl)propane-1,3-diol
• CAS No.: 1395081-64-7
• Molecular Formula: C₂₂H₂₈O₇
• Molecular Weight: 404.46
• Mol file: 1395081-64-7.mol

Synonyms:(1R,2R)-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)-1-(3,4,5-trimethoxyphenyl)propane-1,3-diol

Chemical Property of (1R,2R)-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)-1-(3,4,5-trimethoxyphenyl)propane-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)-1-(3,4,5-trimethoxyphenyl)propane-1,3-diol

There total 7 articles about (1R,2R)-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)-1-(3,4,5-trimethoxyphenyl)propane-1,3-diol 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: 98.0%

(S)-3-((2S,3R)-3-hydroxy-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)-3-(3,4,5-trimethoxyphenyl)propanoyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one (1395081-61-4) → (1R,2R)-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)-1-(3,4,5-trimethoxyphenyl)propane-1,3-diol (1395081-64-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1055/s-0031-1290678

Reference yield:

ethyl 2-(2-methoxy-4-(prop-1-enyl)phenoxy)acetate (632290-89-2) → (1R,2R)-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)-1-(3,4,5-trimethoxyphenyl)propane-1,3-diol (1395081-64-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dichloro bis(acetonitrile) palladium(II) / dichloromethane / 24 h / 20 °C / Inert atmosphere

2.1: sodium hydroxide / methanol; dichloromethane / 3 h / 20 °C / Inert atmosphere

2.2: 0 °C / pH 2 - 3 / Inert atmosphere

3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; toluene / 0.33 h / 0 °C / Inert atmosphere

4.2: 3.33 h / -78 - 20 °C / Inert atmosphere

5.1: di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere

5.2: 0.5 h / 20 °C / Inert atmosphere

5.3: 4.75 h / -78 - 0 °C / Inert atmosphere

6.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 20 °C / Inert atmosphere

With dichloro bis(acetonitrile) palladium(II); lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; N,N-dimethyl-formamide; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 5.1: Aldol condensation / 5.2: Aldol condensation / 5.3: Aldol condensation;

DOI:10.1055/s-0031-1290678

Reference yield:

(S,E)-4-isopropyl-3-(2-(2-methoxy-4-(prop-1-enyl)phenoxy)acetyl)-5,5-diphenyloxazolidin-2-one (1395081-58-9) → (1R,2R)-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)-1-(3,4,5-trimethoxyphenyl)propane-1,3-diol (1395081-64-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere

1.2: 0.5 h / 20 °C / Inert atmosphere

1.3: 4.75 h / -78 - 0 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; di-n-butylboryl trifluoromethanesulfonate; In diethyl ether; dichloromethane; 1.1: Aldol condensation / 1.2: Aldol condensation / 1.3: Aldol condensation;

DOI:10.1055/s-0031-1290678

upstream raw materials:

(S,E)-4-isopropyl-3-(2-(2-methoxy-4-(prop-1-enyl)phenoxy)acetyl)-5,5-diphenyloxazolidin-2-one

(S)-3-((2S,3R)-3-hydroxy-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)-3-(3,4,5-trimethoxyphenyl)propanoyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one

ethyl 2-(2-methoxy-4-(prop-1-enyl)phenoxy)acetate

C₁₄H₁₈O₄

Downstream raw materials:

(2R,3R)-3-hydroxy-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)-3-(3,4,5-trimethoxyphenyl)propyl 4-methylbenzenesulfonate