3-Oxo-14-acetoxy-2α-(phenylseleneyl)-5αH,4,6,11βH-eudesman-12,6-olide

Base Information

• Chemical Name: 3-Oxo-14-acetoxy-2α-(phenylseleneyl)-5αH,4,6,11βH-eudesman-12,6-olide
• CAS No.: 160282-46-2
• Molecular Formula: C₂₃H₂₈O₅Se
• Molecular Weight: 463.432
• Mol file: 160282-46-2.mol

Synonyms:3-Oxo-14-acetoxy-2α-(phenylseleneyl)-5αH,4,6,11βH-eudesman-12,6-olide

Chemical Property of 3-Oxo-14-acetoxy-2α-(phenylseleneyl)-5αH,4,6,11βH-eudesman-12,6-olide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Oxo-14-acetoxy-2α-(phenylseleneyl)-5αH,4,6,11βH-eudesman-12,6-olide

There total 16 articles about 3-Oxo-14-acetoxy-2α-(phenylseleneyl)-5αH,4,6,11βH-eudesman-12,6-olide 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: 96.0%

Phenylselenyl chloride (5707-04-0) + 3-Oxo-14-acetoxy-5αH,4,6,11βH-eudesman-12,6-olide (73719-41-2) → 3-Oxo-14-acetoxy-2α-(phenylseleneyl)-5αH,4,6,11βH-eudesman-12,6-olide (160282-46-2)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; for 20h; Ambient temperature;

DOI:10.1021/jo00100a049

Reference yield:

santonin (481-06-1) → 3-Oxo-14-acetoxy-2α-(phenylseleneyl)-5αH,4,6,11βH-eudesman-12,6-olide (160282-46-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) H₂, 2.) 70percent HClO₄ / 1.) 5percent Pd/CaCO₃ / 1.) EtOAc, 50 deg C, atmospheric pressure, 3 h, 2.) EtOH, 80 deg C, 1 h

2: 99 percent / conc. H₂SO₄ / 3.5 h / Heating

3: 93 percent / m-CPBA / CHCl₃ / 48 h / 0 °C

4: 100 percent / 0.08 h / 160 °C

5: 76 percent / aq. K₂CO₃ / propan-2-ol / 11 h / Ambient temperature

6: 87 percent / NaBH₄ / methanol / 0.08 h / Ambient temperature

7: 84 percent / mercury oxide, I₂ / cyclohexane / 8 h / Heating; Irradiation

8: 5percent methanolic KOH / 6 h / Ambient temperature

9: 75 percent / PCC / CH₂Cl₂ / 6 h / Ambient temperature

10: 63 percent / ZnI₂ / CH₂Cl₂ / 24 h / Ambient temperature

11: 96 percent / BF₃*Et₂O / tetrahydrofuran; CH₂Cl₂ / 20 h / Ambient temperature

With potassium hydroxide; sodium tetrahydroborate; perchloric acid; sulfuric acid; boron trifluoride diethyl etherate; hydrogen; iodine; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; mercury(II) oxide; zinc(II) iodide; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; chloroform; cyclohexane; isopropyl alcohol;

DOI:10.1021/jo00100a049

Reference yield:

2-Oxo-3β-acetoxy-5αH,4,6,11βH-eudesman-12,6-olide (41720-80-3) → 3-Oxo-14-acetoxy-2α-(phenylseleneyl)-5αH,4,6,11βH-eudesman-12,6-olide (160282-46-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / NaBH₄ / methanol / 0.08 h / Ambient temperature

2: 84 percent / mercury oxide, I₂ / cyclohexane / 8 h / Heating; Irradiation

3: 5percent methanolic KOH / 6 h / Ambient temperature

4: 75 percent / PCC / CH₂Cl₂ / 6 h / Ambient temperature

5: 63 percent / ZnI₂ / CH₂Cl₂ / 24 h / Ambient temperature

6: 96 percent / BF₃*Et₂O / tetrahydrofuran; CH₂Cl₂ / 20 h / Ambient temperature

With potassium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; iodine; pyridinium chlorochromate; mercury(II) oxide; zinc(II) iodide; In tetrahydrofuran; methanol; dichloromethane; cyclohexane;

DOI:10.1021/jo00100a049

upstream raw materials:

Phenylselenyl chloride

3-Oxo-14-acetoxy-5αH,4,6,11βH-eudesman-12,6-olide

2-Oxo-3β-acetoxy-5αH,4,6,11βH-eudesman-12,6-olide

6β-Hydroxy-3-oxo-5,6α(H)-4,11β(H)-eudesman-saeure-(13)