4H-1-Benzopyran-4-one, 3,5,7-tris(acetyloxy)-2-[3-[4-(acetyloxy)-3-methoxyphenyl]-2,3-dihydro-2- (hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-, (2R,3R)-

Base Information

• Chemical Name: 4H-1-Benzopyran-4-one, 3,5,7-tris(acetyloxy)-2-[3-[4-(acetyloxy)-3-methoxyphenyl]-2,3-dihydro-2- (hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-, (2R,3R)-
• CAS No.: 802918-29-2
• Molecular Formula: C33H30O14
• Molecular Weight: 650.593
• Mol file: 802918-29-2.mol

Synonyms:

Chemical Property of 4H-1-Benzopyran-4-one, 3,5,7-tris(acetyloxy)-2-[3-[4-(acetyloxy)-3-methoxyphenyl]-2,3-dihydro-2- (hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-, (2R,3R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4H-1-Benzopyran-4-one, 3,5,7-tris(acetyloxy)-2-[3-[4-(acetyloxy)-3-methoxyphenyl]-2,3-dihydro-2- (hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-, (2R,3R)-

There total 5 articles about 4H-1-Benzopyran-4-one, 3,5,7-tris(acetyloxy)-2-[3-[4-(acetyloxy)-3-methoxyphenyl]-2,3-dihydro-2- (hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-, (2R,3R)- 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: 80.0%

3,5,7,20-O-tetra-acetyl-23-O-(4,4'-dimethoxytriphenylmethyl)-silybin (1326308-17-1) → 3,5,7-triacetoxy-2-[3-(4-acetoxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chroman-4-one (802918-29-2)

Guidance literature:

With formic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/j.bmcl.2011.06.049

Reference yield:

Acetic acid (2R,3R)-3,7-diacetoxy-2-[3-(4-acetoxy-3-methoxy-phenyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-benzo[1,4]dioxin-6-yl]-4-oxo-chroman-5-yl ester → 3,5,7-triacetoxy-2-[3-(4-acetoxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chroman-4-one (802918-29-2)

Guidance literature:

With boron trifluoride diethyl etherate; In chloroform; at 20 ℃; for 12h;

DOI:10.1016/j.bmc.2004.07.064

Reference yield:

silybin (802918-57-6) → 3,5,7-triacetoxy-2-[3-(4-acetoxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chroman-4-one (802918-29-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / AgNO₃; pyridine / 2 h / 40 °C

2: pyridine / 24 h / 20 °C

3: 535 mg / boron trifuoride etherate / CHCl₃ / 12 h / 20 °C

With pyridine; boron trifluoride diethyl etherate; silver nitrate; In chloroform;

DOI:10.1016/j.bmc.2004.07.064

upstream raw materials:

silybin

2-(2-{[(tert-butyldimethylsilyl)oxy]methyl}-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl)-3,5,7-trihydroxychroman-4-one

23-O-(4,4’-dimethoxytriphenylmethyl)silibinin

3,5,7,20-O-tetra-acetyl-23-O-(4,4'-dimethoxytriphenylmethyl)-silybin

Downstream raw materials:

sodium silybin-23-O-(4-nitrophenyl)-phosphate

23-amine-silybin

23-azide-silybin

C₃₁H₂₆NO₁₅P