Bisisorhapontigenin A

Base Information

• Chemical Name: Bisisorhapontigenin A
• CAS No.: 865474-98-2
• Molecular Formula: C₃₀H₂₆O₈
• Molecular Weight: 514.532
• Mol file: 865474-98-2.mol

Synonyms:

Chemical Property of Bisisorhapontigenin A

Chemical Property:

• Boiling Point: 723.8±60.0 °C(Predicted)
• PKA: 9.26±0.10(Predicted)
• Density: 1.424±0.06 g/cm3(Predicted)

Purity/Quality:

99%+, ^*data from raw suppliers

BisisorhapontigeninA ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bisisorhapontigenin A

There total 6 articles about Bisisorhapontigenin A 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: 85.0%

C30H24Br2O8 → 6-hydroxy-3-(3,5-dihydroxyphenyl)-2-(3-methoxy-4-hydroxyphenyl)-4-(E)-(3-methoxy-4-hydroxystyryl)-2,3-dihydrobenzofuran (865474-98-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 18h; Inert atmosphere;

DOI:10.1055/s-0037-1611713

Reference yield:

isorhapontigenin (32507-66-7) → bisisorhapontigenin B + 6-hydroxy-3-(3,5-dihydroxyphenyl)-2-(3-methoxy-4-hydroxyphenyl)-4-(E)-(3-methoxy-4-hydroxystyryl)-2,3-dihydrobenzofuran (865474-98-2) + 6-hydroxy-2-(3,5-dihydroxyphenyl)-3-(3-methoxy-4-hydroxyphenyl)-4-(E)-(3-methoxy-4-hydroxystyryl)-2,3-dihydrobenzofuran + 5,11-bis(3-methoxy-4-hydroxyphenyl)-2,4,8,10-tetrahydroxydibenzo[a,e]-tetrahydropentalene

Guidance literature:

With iron(III) chloride; In acetone; at 20 ℃; for 36h; Further byproducts given;

DOI:10.1248/cpb.52.238

Reference yield:

5-bromo-4-hydroxy-3-methoxybenzaldehyde (2973-76-4) → 6-hydroxy-3-(3,5-dihydroxyphenyl)-2-(3-methoxy-4-hydroxyphenyl)-4-(E)-(3-methoxy-4-hydroxystyryl)-2,3-dihydrobenzofuran (865474-98-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / toluene; hexane / 0.5 h / Inert atmosphere

1.2: Wittig Olefination / 5 h / 110 °C / Reflux

2.1: N,N-dimethyl-aniline / dichloromethane / 0.08 h / 0 °C

2.2: 3 h / 20 °C

3.1: iron(III) chloride trihydrate / acetone / 8 h / 20 °C / Darkness; Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / Inert atmosphere

With lithium aluminium tetrahydride; n-butyllithium; iron(III) chloride trihydrate; N,N-dimethyl-aniline; In tetrahydrofuran; hexane; dichloromethane; acetone; toluene;

DOI:10.1055/s-0037-1611713

upstream raw materials:

isorhapontigenin

5-bromo-4-hydroxy-3-methoxybenzaldehyde

Refernces

• 1、 Guan, Xingchao,Liu, Meijie,Shao, Zhibo,Li, Hongpeng,Ran, Lu,Li, Wenling. "Efficient Synthesis of Several Natural Oligostilbenes from the Biomimetic Oxidation of Brominated Isorhapontigenin". . p. 1825 - 1831. Retrieved 2019.