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

Base Information

• Chemical Name: 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
• CAS No.: 802918-28-1
• Molecular Formula: C₃₁H₃₆O₁₀Si
• Molecular Weight: 596.706
• Mol file: 802918-28-1.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 1 articles about 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 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: 67.0%

silybin (802918-57-6) + tert-butyldimethylsilyl chloride (18162-48-6) → 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 (802918-28-1)

Guidance literature:

With pyridine; silver nitrate; at 40 ℃; for 2h;

DOI:10.1016/j.bmc.2004.07.064

Reference yield:

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 (802918-28-1) → 3-(4-hydroxy-3-methoxyphenyl)-6-(3,5,7-trihydroxy-4-oxochroman-2-yl)-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 24 h / 20 °C

2: 535 mg / boron trifuoride etherate / CHCl₃ / 12 h / 20 °C

3: 77 percent / H₅IO₆/CrO₃ / acetonitrile; H₂O / 0.75 h / 0 °C

4: 70 percent / K₂CO₃ / methanol; H₂O / 24 h / 20 °C

With pyridine; chromium(VI) oxide; boron trifluoride diethyl etherate; potassium carbonate; periodic acid; In methanol; chloroform; water; acetonitrile;

DOI:10.1016/j.bmc.2004.07.064

Reference yield:

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 (802918-28-1) → 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:

Multi-step reaction with 2 steps

1: pyridine / 24 h / 20 °C

2: 535 mg / boron trifuoride etherate / CHCl₃ / 12 h / 20 °C

With pyridine; boron trifluoride diethyl etherate; In chloroform;

DOI:10.1016/j.bmc.2004.07.064

upstream raw materials:

silybin

tert-butyldimethylsilyl chloride

Downstream raw materials:

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

3-(4-acetoxy-3-methoxyphenyl)-6-[3,5,7-triacetoxy-4-oxochroman-2-yl]-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid