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

Base Information

• Chemical Name: (2R,3R)-3-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)propyl-4-methylbenzenesulfonate
• CAS No.: 1395081-66-9
• Molecular Formula: C₂₈H₃₂O₈S
• Molecular Weight: 528.623
• Mol file: 1395081-66-9.mol

Synonyms:(2R,3R)-3-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)propyl-4-methylbenzenesulfonate

Chemical Property of (2R,3R)-3-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)propyl-4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)propyl-4-methylbenzenesulfonate

There total 7 articles about (2R,3R)-3-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)propyl-4-methylbenzenesulfonate 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: 96.0%

(1R,2R)-1-(3,4-dimethoxyphenyl)-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)propane-1,3-diol (1395081-63-6) + p-toluenesulfonyl chloride (98-59-9) → (2R,3R)-3-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)propyl-4-methylbenzenesulfonate (1395081-66-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1055/s-0031-1290678

Reference yield:

ethyl 2-(2-methoxy-4-(prop-1-enyl)phenoxy)acetate (632290-89-2) → (2R,3R)-3-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)propyl-4-methylbenzenesulfonate (1395081-66-9)

Guidance literature:

Multi-step reaction with 7 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

7.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With dmap; dichloro bis(acetonitrile) palladium(II); lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; triethylamine; 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) → (2R,3R)-3-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxy-4-((E)-prop-1-enyl)phenoxy)propyl-4-methylbenzenesulfonate (1395081-66-9)

Guidance literature:

Multi-step reaction with 3 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

3.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With dmap; lithium aluminium tetrahydride; di-n-butylboryl trifluoromethanesulfonate; triethylamine; 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

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

p-toluenesulfonyl chloride

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