(3R,3aR,6aR,9aR,9bR)-3,6-Dimethyl-9-methylene-3-phenylselanyl-3a,4,6a,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

Base Information

• Chemical Name: (3R,3aR,6aR,9aR,9bR)-3,6-Dimethyl-9-methylene-3-phenylselanyl-3a,4,6a,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
• CAS No.: 90807-56-0
• Molecular Formula: C₂₁H₂₄O₂Se
• Molecular Weight: 387.38
• Mol file: 90807-56-0.mol

Synonyms:

Chemical Property of (3R,3aR,6aR,9aR,9bR)-3,6-Dimethyl-9-methylene-3-phenylselanyl-3a,4,6a,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,3aR,6aR,9aR,9bR)-3,6-Dimethyl-9-methylene-3-phenylselanyl-3a,4,6a,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

There total 5 articles about (3R,3aR,6aR,9aR,9bR)-3,6-Dimethyl-9-methylene-3-phenylselanyl-3a,4,6a,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one 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:

1-oxo-Δ2-santenolide (58698-14-9) → (3R,3aR,6aR,9aR,9bR)-3,6-Dimethyl-9-methylene-3-phenylselanyl-3a,4,6a,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one (90807-56-0)

Guidance literature:

Multi-step reaction with 5 steps

2: 93 percent / Zn-Hg / acetic acid / 1 h / Heating

3: 81 percent / LiAl(t-BuO)3H / tetrahydrofuran / 1 h / 0 °C

4: 97 percent / Py / 3.5 h / 25 °C

With pyridine; lithium tri-t-butoxyaluminum hydride; mercury; zinc; In tetrahydrofuran; acetic acid;

DOI:10.1021/np980092u

Reference yield:

11β,13-dihydroreynosin (32223-12-4) → (3R,3aR,6aR,9aR,9bR)-3,6-Dimethyl-9-methylene-3-phenylselanyl-3a,4,6a,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one (90807-56-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / Py / 3.5 h / 25 °C

With pyridine;

DOI:10.1021/np980092u

Reference yield:

diphenyl diselenide (1666-13-3) + 1β-Mesyloxyeudesm-4(14)-eno-13,6α-lactone (90807-53-7) → (3R,3aR,9aS,9bR)-3,6-Dimethyl-9-methylene-3-phenylselanyl-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one (90807-58-2) + (3R,3aR,6aR,9aR,9bR)-3,6-Dimethyl-9-methylene-3-phenylselanyl-3a,4,6a,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one (90807-56-0) + 11β,13-dehydrocostuslactone (4955-03-7)

Guidance literature:

With potassium acetate; lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1.) acetic acid, reflux; 2.) THF, HMPA, -78 deg C;

DOI:10.1246/cl.1984.493

upstream raw materials:

diphenyl diselenide

1β-Mesyloxyeudesm-4(14)-eno-13,6α-lactone

11β,13-dihydroreynosin

1-oxo-Δ²-santenolide

Downstream raw materials:

eremanthine