2'',4''-Diacetylafzelin

Base Information

• Chemical Name: 2'',4''-Diacetylafzelin
• CAS No.: 133882-73-2
• Molecular Formula: C₂₅H₂₄O₁₂
• Molecular Weight: 516.458
• Wikidata: Q110191712
• Mol file: 133882-73-2.mol

Synonyms:2'',4''-Diacetylafzelin;CHEBI:176209;[5-acetyloxy-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-4-hydroxy-2-methyloxan-3-yl] acetate

Chemical Property of 2'',4''-Diacetylafzelin

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 7
• Exact Mass: 516.12677620
• Heavy Atom Count: 37
• Complexity: 909

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)OC(=O)C)O)OC(=O)C

Technology Process of 2'',4''-Diacetylafzelin

There total 14 articles about 2'',4''-Diacetylafzelin 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: 88.0%

(2S,3R,4R,5R,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl diacetate (916069-07-3) → Kaempferol-3-O-(2,4-di-O-acetyl-alpha-L-rhamnopyranoside) (133882-73-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol; at 20 ℃; for 3h;

DOI:10.1021/ol062076r

Reference yield:

tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate (865484-73-7) → Kaempferol-3-O-(2,4-di-O-acetyl-alpha-L-rhamnopyranoside) (133882-73-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 85 percent / PPh₃ / Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 3 h / 0 °C

2.1: 73 percent / NaBH₄ / CH₂Cl₂; methanol / 3 h / -78 °C

3.1: 156 mg / pyridine; DMAP / CH₂Cl₂ / 1 h / 0 °C

4.1: 77 percent / OsO₄; NMO / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

5.1: p-TsOH*H₂O / CH₂Cl₂ / 0.25 h / 0 °C

5.2: 99 percent / aq. HOAc / CH₂Cl₂ / 0.25 h / 0 °C

6.1: 88 percent / H₂ / Pd/C / tetrahydrofuran; ethanol / 3 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; hydrogen; toluene-4-sulfonic acid; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/ol062076r

Reference yield:

5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one (23405-70-1) → Kaempferol-3-O-(2,4-di-O-acetyl-alpha-L-rhamnopyranoside) (133882-73-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 85 percent / PPh₃ / Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 3 h / 0 °C

2.1: 73 percent / NaBH₄ / CH₂Cl₂; methanol / 3 h / -78 °C

3.1: 156 mg / pyridine; DMAP / CH₂Cl₂ / 1 h / 0 °C

4.1: 77 percent / OsO₄; NMO / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

5.1: p-TsOH*H₂O / CH₂Cl₂ / 0.25 h / 0 °C

5.2: 99 percent / aq. HOAc / CH₂Cl₂ / 0.25 h / 0 °C

6.1: 88 percent / H₂ / Pd/C / tetrahydrofuran; ethanol / 3 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; hydrogen; toluene-4-sulfonic acid; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/ol062076r

upstream raw materials:

(2S,3R,4R,5R,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl diacetate

tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate

5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one

3-((2S,6S)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yloxy)-5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one

Downstream raw materials:

kaempferol 3-rhamnoside