paeoniflorigenin

Base Information

• Chemical Name: paeoniflorigenin
• CAS No.: 697300-41-7
• Molecular Formula: C₁₇H₁₈O₆
• Molecular Weight: 318.326
• Mol file: 697300-41-7.mol

Synonyms:

Chemical Property of paeoniflorigenin

Chemical Property:

Purity/Quality:

≥98% ^*data from raw suppliers

Paeoniflorgenin 96.51% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of paeoniflorigenin

There total 37 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 (697300-41-7)

Guidance literature:

Multi-step reaction with 23 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: ZnCl₂, AgClO₄, 4A molecular sieves / benzene / 6 h / Ambient temperature

15: 100 percent / H₂ / Pd(OH)2/C / methanol / 2 h / 760 Torr

16: 92 percent / HF / acetonitrile / 10 h / Ambient temperature

17: 91 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 48 h / 23 °C

18: 69 percent / pyridine / 15 h / 0 °C

19: 85 percent / HF / acetonitrile / 0.17 h / 0 °C

20: 90 percent / PPh₃, I₂, imidazole / benzene / 2 h / Heating

21: 85 percent / 2,6-lutidine / CH₂Cl₂ / 10 h / Ambient temperature

22: 93 percent / Zn / ethanol; H₂O / 2 h / Heating

23: HF / acetonitrile / 2 h / Ambient temperature

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; dmap; samarium diiodide; trifluoromethane sulfonyl chloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; Mn₃O(OAc)7; hydrogen fluoride; hydrogen; iodine; potassium acetate; silver perchlorate; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; zinc(II) chloride; zinc; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetonitrile; benzene;

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 (697300-41-7)

Guidance literature:

Multi-step reaction with 22 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: ZnCl₂, AgClO₄, 4A molecular sieves / benzene / 6 h / Ambient temperature

14: 100 percent / H₂ / Pd(OH)2/C / methanol / 2 h / 760 Torr

15: 92 percent / HF / acetonitrile / 10 h / Ambient temperature

16: 91 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 48 h / 23 °C

17: 69 percent / pyridine / 15 h / 0 °C

18: 85 percent / HF / acetonitrile / 0.17 h / 0 °C

19: 90 percent / PPh₃, I₂, imidazole / benzene / 2 h / Heating

20: 85 percent / 2,6-lutidine / CH₂Cl₂ / 10 h / Ambient temperature

21: 93 percent / Zn / ethanol; H₂O / 2 h / Heating

22: HF / acetonitrile / 2 h / Ambient temperature

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; dmap; samarium diiodide; trifluoromethane sulfonyl chloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen fluoride; hydrogen; iodine; silver perchlorate; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; zinc(II) chloride; zinc; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetonitrile; benzene;

DOI:10.1021/ja00072a063

upstream raw materials:

C₂₆H₃₈O₆Si

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

C₂₂H₄₂O₅Si₂

C₁₉H₃₁NO₄Si