7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin

Base Information

• Chemical Name: 7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin
• CAS No.: 679398-77-7
• Molecular Formula: C₃₅H₄₄O₁₄Si
• Molecular Weight: 716.811
• Mol file: 679398-77-7.mol

Synonyms:7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin

Chemical Property of 7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin

There total 2 articles about 7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin 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: 71.0%

2-(4-hydroxyphenyl)-5-hydroxy-7-(tert-butyldimethylsiloxy)chroman-4-one (679398-75-5) + 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose (439-03-2,439-04-3,439-05-4,2823-44-1,2823-46-3,3934-29-0,4163-44-4,4163-45-5,20409-31-8,23235-96-3,51897-75-7,51897-76-8,51897-77-9,57573-38-3,62561-28-8,126641-47-2) → 4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin (679398-78-8) + 7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin (679398-77-7)

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2004.01.001

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin (679398-77-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / imidazole / dimethylformamide / 13 h / 20 °C

2: 71 percent / 2,6-di-tert-butyl-4-methylpyridine; BF₃*Et₂O / CH₂Cl₂ / 1 h / 20 °C

With 1H-imidazole; 2,6-di-tert-butyl-4-methylpyridine; boron trifluoride diethyl etherate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.01.001

Reference yield: 9.0%

7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin (679398-77-7) → 7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin (679398-80-2)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 110 ℃; for 17h;

DOI:10.1016/j.tet.2004.01.001

upstream raw materials:

2-(4-hydroxyphenyl)-5-hydroxy-7-(tert-butyldimethylsiloxy)chroman-4-one

2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose

tert-butyldimethylsilyl chloride

Downstream raw materials:

7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin

apigenin-4'-O-β-D-glucopyranoside

4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin