14-(3-hydroxy-4-methoxyphenyl)-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-3-yl 2,2,2-trichloroethyl sulfate

Base Information

• Chemical Name: 14-(3-hydroxy-4-methoxyphenyl)-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-3-yl 2,2,2-trichloroethyl sulfate
• CAS No.: 895632-77-6
• Molecular Formula: C₃₁H₂₄Cl₃NO₁₁S
• Molecular Weight: 724.957
• Mol file: 895632-77-6.mol

Synonyms:14-(3-hydroxy-4-methoxyphenyl)-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-3-yl 2,2,2-trichloroethyl sulfate

Chemical Property of 14-(3-hydroxy-4-methoxyphenyl)-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-3-yl 2,2,2-trichloroethyl sulfate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 14-(3-hydroxy-4-methoxyphenyl)-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-3-yl 2,2,2-trichloroethyl sulfate

There total 32 articles about 14-(3-hydroxy-4-methoxyphenyl)-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-3-yl 2,2,2-trichloroethyl sulfate 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%

2,2,2-trichloroethyl 2,11,12-trimethoxy-14-[4-methoxy-3-(methoxymethoxy)phenyl]-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-3-yl sulfate (1225441-65-5) → 14-(3-hydroxy-4-methoxyphenyl)-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-3-yl 2,2,2-trichloroethyl sulfate (895632-77-6)

Guidance literature:

With hydrogenchloride; In methanol; at 30 ℃; for 12h;

DOI:10.1016/j.bmc.2011.10.030

Reference yield: 96.0%

sulfuric acid 13-(3-isopropoxy-4-methoxy-phenyl)-2,10,11-trimethoxy-6-oxo-6H-5-oxa-6b-aza-dibenzo[a,i]fluoren-3-yl ester 2,2,2-trichloro-ethyl ester (895632-76-5) → 14-(3-hydroxy-4-methoxyphenyl)-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-3-yl 2,2,2-trichloroethyl sulfate (895632-77-6)

Guidance literature:

With boron trichloride; In dichloromethane; at -78 - 0 ℃; for 4.5h;

DOI:10.1016/j.tetlet.2006.03.121

Reference yield:

5-bromo-2-methoxyphenol (37942-01-1) → 14-(3-hydroxy-4-methoxyphenyl)-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-3-yl 2,2,2-trichloroethyl sulfate (895632-77-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: potassium carbonate / acetone / 9 h / Inert atmosphere; Reflux

2.1: tert.-butyl lithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 - 20 °C

2.3: pH 3

3.1: dichloromethane / 26 h / 20 °C

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; water / 3 h / Reflux; Inert atmosphere

5.1: potassium hydroxide / ethanol; water / 2 h / Reflux

6.1: pyridinium p-toluenesulfonate / dichloromethane / 8 h / Reflux

7.1: quinoline; copper(II) oxide / 0.17 h / 220 °C / Inert atmosphere

8.1: boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene / dichloromethane / 1.5 h / -40 °C / Inert atmosphere

9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 30 h / Reflux

10.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 7 h / 20 °C

11.1: dmap; triethylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere

12.1: hydrogenchloride / methanol / 12 h / 30 °C

With quinoline; hydrogenchloride; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium carbonate; potassium carbonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; copper(II) oxide; potassium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone; 4.1: Suzuki-Miyaura coupling;

DOI:10.1016/j.bmc.2011.10.030

upstream raw materials:

sulfuric acid 13-(3-isopropoxy-4-methoxy-phenyl)-2,10,11-trimethoxy-6-oxo-6H-5-oxa-6b-aza-dibenzo[a,i]fluoren-3-yl ester 2,2,2-trichloro-ethyl ester

3-hydroxy-13-(3-isopropoxy-4-methoxy-phenyl)-2,10,11-trimethoxy-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one

1-[2-(3,4-dimethoxy-phenyl)-ethyl]-3-(3-isopropoxy-4-methoxy-phenyl)-4-trifluoromethanesulfonyloxy-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester

20-benzyl-13-isopropyllamellarin α

Refernces

• 1、 Fukuda, Tsutomu,Ohta, Takeshi,Saeki, Sho,Iwao, Masatomo. "Divergent synthesis of lamellarin α 13-sulfate, 20-sulfate, and 13,20-disulfate". scheme or table. p. 841 - 846. Retrieved 2010/10/05.