(+/-)-paeoniflorigenin

Base Information

• Chemical Name: (+/-)-paeoniflorigenin
• CAS No.: 151559-78-3
• Molecular Formula: C₁₇H₁₈O₆
• Molecular Weight: 318.326
• Mol file: 151559-78-3.mol

Synonyms:(+/-)-paeoniflorigenin

Chemical Property of (+/-)-paeoniflorigenin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-paeoniflorigenin

There total 13 articles about (+/-)-paeoniflorigenin 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: 91.0%

C26H38O6Si (151559-90-9,151635-94-8) → (+/-)-paeoniflorigenin (151559-78-3,697300-41-7)

Guidance literature:

With hydrogen fluoride; In acetonitrile; for 2h; Ambient temperature;

DOI:10.1021/ja00072a063

Reference yield:

triisopropyl((5-methylcyclohexa-1,4-dien-1-yl)oxy)silane (151559-79-4) → (+/-)-paeoniflorigenin (151559-78-3,697300-41-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 48 percent / Mn₃O(OAc)7, AcOK / acetonitrile / 15 h / Ambient temperature

2: 70 percent / CF₃SO₂Cl, Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

3: 81 percent / mCPBA, NaHCO₃ / CH₂Cl₂ / 15 h / Ambient temperature

4: 78 percent / diisobutylaluminum hydride / CH₂Cl₂ / 0.5 h / -78 °C

5: 35 percent / trimethylsilyl triflate / CH₂Cl₂ / 1 h / -78 °C

6: 100 percent / pyridinium chlorochromate, 4A molecular sieves / 0.5 h / Ambient temperature

7: 93 percent / SmI₂ / tetrahydrofuran / 10 h / -45 °C

8: 82 percent / CH₂Cl₂ / 15 h / Heating

9: 86 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

10: 81 percent / DIBAL / CH₂Cl₂ / 0.02 h / -78 °C

11: 96 percent / pyridine / CH₂Cl₂ / 3 h / Heating

12: 100 percent / 1 N HCl / tetrahydrofuran / 6 h / 0 °C

13: 91 percent / HF / acetonitrile / 2 h / Ambient temperature

With pyridine; hydrogenchloride; samarium diiodide; trifluoromethane sulfonyl chloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; Mn₃O(OAc)7; hydrogen fluoride; potassium acetate; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/ja00072a063

Reference yield:

(3aS,7aR)-6-Methyl-2-oxo-7a-triisopropylsilanyloxy-2,3,3a,4,7,7a-hexahydro-benzofuran-3-carbonitrile → (+/-)-paeoniflorigenin (151559-78-3,697300-41-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 70 percent / CF₃SO₂Cl, Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

2: 81 percent / mCPBA, NaHCO₃ / CH₂Cl₂ / 15 h / Ambient temperature

3: 78 percent / diisobutylaluminum hydride / CH₂Cl₂ / 0.5 h / -78 °C

4: 35 percent / trimethylsilyl triflate / CH₂Cl₂ / 1 h / -78 °C

5: 100 percent / pyridinium chlorochromate, 4A molecular sieves / 0.5 h / Ambient temperature

6: 93 percent / SmI₂ / tetrahydrofuran / 10 h / -45 °C

7: 82 percent / CH₂Cl₂ / 15 h / Heating

8: 86 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

9: 81 percent / DIBAL / CH₂Cl₂ / 0.02 h / -78 °C

10: 96 percent / pyridine / CH₂Cl₂ / 3 h / Heating

11: 100 percent / 1 N HCl / tetrahydrofuran / 6 h / 0 °C

12: 91 percent / HF / acetonitrile / 2 h / Ambient temperature

With pyridine; hydrogenchloride; samarium diiodide; trifluoromethane sulfonyl chloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen fluoride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/ja00072a063

upstream raw materials:

C₂₆H₃₈O₆Si

triisopropyl((5-methylcyclohexa-1,4-dien-1-yl)oxy)silane

C₂₂H₄₂O₅Si₂

C₁₉H₃₁NO₄Si