3α,4α-epoxy-11β(H)-eudesman-8,13-olide

Base Information

• Chemical Name: 3α,4α-epoxy-11β(H)-eudesman-8,13-olide
• CAS No.: 58511-26-5
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.338
• Mol file: 58511-26-5.mol

Synonyms:

Chemical Property of 3α,4α-epoxy-11β(H)-eudesman-8,13-olide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3α,4α-epoxy-11β(H)-eudesman-8,13-olide

There total 1 articles about 3α,4α-epoxy-11β(H)-eudesman-8,13-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: 19.0%

3,3-ethanedithio-11α(H)-eudesm-4,5-dien-8,13-olide (89362-29-8) → 3α,4α-epoxy-11β(H)-eudesman-8,13-olide (58511-26-5) + tetrahydroalantolactone (58526-58-2)

Guidance literature:

With W-2 Raney Ni; 3-chloro-benzenecarboperoxoic acid; In ethanol; at 40 ℃; for 0.416667h; Yields of byproduct given;

DOI:10.1248/cpb.31.3411

Reference yield:

3α,4α-epoxy-11β(H)-eudesman-8,13-olide (58511-26-5) → (3S,3aS,4aR,8aR,9aR)-4a-Hydroxy-3,8a-dimethyl-5-methylene-3-phenylselanyl-decahydro-naphtho[2,3-b]furan-2-one (89293-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 57 percent / Et₂NH/15percent n-BuLi / diethyl ether; hexane / 3 h / Heating

2: 17 percent / 1.) LDA; 2.) hexamethylphosphoramide (HMPA) / tetrahydrofuran / 2.5 h / -78 - -50 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1248/cpb.31.3411

Reference yield:

3α,4α-epoxy-11β(H)-eudesman-8,13-olide (58511-26-5) → telekin (6752-90-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 57 percent / Et₂NH/15percent n-BuLi / diethyl ether; hexane / 3 h / Heating

2: 17 percent / 1.) LDA; 2.) hexamethylphosphoramide (HMPA) / tetrahydrofuran / 2.5 h / -78 - -50 °C

3: 64 percent / 35percent H₂O₂ / tetrahydrofuran / 0.5 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; dihydrogen peroxide; diethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1248/cpb.31.3411

upstream raw materials:

3,3-ethanedithio-11α(H)-eudesm-4,5-dien-8,13-olide

Downstream raw materials:

telekin

(3S,3aS,4aR,8aR,9aR)-4a-Hydroxy-3,8a-dimethyl-5-methylene-3-phenylselanyl-decahydro-naphtho[2,3-b]furan-2-one