(+/-)-(7E,9Z)-trisporol

Base Information

• Chemical Name: (+/-)-(7E,9Z)-trisporol
• CAS No.: 69854-99-5
• Molecular Formula: C₁₈H₂₆O₃
• Molecular Weight: 290.403
• Mol file: 69854-99-5.mol

Synonyms:(+/-)-(7E,9Z)-trisporol

Chemical Property of (+/-)-(7E,9Z)-trisporol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-(7E,9Z)-trisporol

There total 25 articles about (+/-)-(7E,9Z)-trisporol 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: 54.0%

trisporol B acetate (69841-86-7) → (+/-)-(7E,9Z)-trisporol (69854-99-5)

Guidance literature:

With potassium carbonate; In ethanol; at 0 - 20 ℃; for 13h;

DOI:10.1021/jo00225a049

Reference yield:

(Z)-2-methyl-5-(2-methyl-[1,3]dioxolan-2-yl)-pent-2-en-1-ol (68965-53-7) → (+/-)-(7E,9Z)-trisporol (69854-99-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 82 percent / hexamethylphosphoramide, methyllithium, p-toluenesulfonyl chloride, LiCl / diethyl ether / 19 h / Ambient temperature

2: 91 percent / NaBr / dimethylformamide / 5 h / Ambient temperature

3: 1.) NaH, 2.) n-butyllithium

4: 94 percent / triethylamine / tetrahydrofuran / 6 h / Heating

5: 71 percent / p-toluenesulfonic acid / benzene / 27 h / Heating

6: triethyl orthoformate, p-toluenesulfonic acid / diethyl ether / 37 h / Ambient temperature

7: LiAlH₄ / tetrahydrofuran / 22 h / Ambient temperature

8: 315 mg / acetic acid, water / 4.5 h / Ambient temperature

9: 79 percent / pyridine / diethyl ether / 22 h / Ambient temperature

10: 94 percent / pyridine / 12 h / Ambient temperature

11: 34 percent / dimethylsulfoxide / 2 h / 80 °C

12: 54 percent / 0.5 M aq. K₂CO₃ / ethanol / 13 h / 0 - 20 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; water; methyllithium; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; orthoformic acid triethyl ester; p-toluenesulfonyl chloride; sodium bromide; lithium chloride; In tetrahydrofuran; diethyl ether; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00225a049

Reference yield:

3-methyl-furan-2,4-dione (1192-51-4,69841-77-6) → (+/-)-(7E,9Z)-trisporol (69854-99-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) NaH, 2.) n-butyllithium

2: 94 percent / triethylamine / tetrahydrofuran / 6 h / Heating

3: 71 percent / p-toluenesulfonic acid / benzene / 27 h / Heating

4: triethyl orthoformate, p-toluenesulfonic acid / diethyl ether / 37 h / Ambient temperature

5: LiAlH₄ / tetrahydrofuran / 22 h / Ambient temperature

6: 315 mg / acetic acid, water / 4.5 h / Ambient temperature

7: 79 percent / pyridine / diethyl ether / 22 h / Ambient temperature

8: 94 percent / pyridine / 12 h / Ambient temperature

9: 34 percent / dimethylsulfoxide / 2 h / 80 °C

10: 54 percent / 0.5 M aq. K₂CO₃ / ethanol / 13 h / 0 - 20 °C

With pyridine; lithium aluminium tetrahydride; n-butyllithium; water; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; orthoformic acid triethyl ester; In tetrahydrofuran; diethyl ether; ethanol; dimethyl sulfoxide; benzene;

DOI:10.1021/jo00225a049

upstream raw materials:

trisporol B acetate

(+/-)-6-hydroxymethyl-2,6-dimethyl-2-cyclohexen-1-one

4-Hydroxymethyl-2,4-dimethyl-3-((E)-3-oxo-but-1-enyl)-cyclohex-2-enone

(+/-)-4-(6'-hydroxymethyl-2',6'-dimethyl-3'-oxo-1'-cyclohexen-1'-yl)-3-butyn-2-ol

Downstream raw materials:

(7E,9Z)-trisporic acid B