(1α,6aβ,7aβ)-(+/-)-decahydro-5,5,7-trimethyl-3-(phenylmethoxy)cyclopenta<6,7>cyclooct<1,2-b>oxirene

Base Information

• Chemical Name: (1α,6aβ,7aβ)-(+/-)-decahydro-5,5,7-trimethyl-3-(phenylmethoxy)cyclopenta<6,7>cyclooct<1,2-b>oxirene
• CAS No.: 90414-06-5
• Molecular Formula: C₂₁H₃₀O₂
• Molecular Weight: 314.468
• Mol file: 90414-06-5.mol

Synonyms:(1α,6aβ,7aβ)-(+/-)-decahydro-5,5,7-trimethyl-3-(phenylmethoxy)cyclopenta<6,7>cyclooct<1,2-b>oxirene

Chemical Property of (1α,6aβ,7aβ)-(+/-)-decahydro-5,5,7-trimethyl-3-(phenylmethoxy)cyclopenta<6,7>cyclooct<1,2-b>oxirene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1α,6aβ,7aβ)-(+/-)-decahydro-5,5,7-trimethyl-3-(phenylmethoxy)cyclopenta<6,7>cyclooct<1,2-b>oxirene

There total 28 articles about (1α,6aβ,7aβ)-(+/-)-decahydro-5,5,7-trimethyl-3-(phenylmethoxy)cyclopenta<6,7>cyclooct<1,2-b>oxirene 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:

(1β,9aβ)-(+/-)-1,2,3,5,7,8,9,9a-octahydro-6-(phenylmethoxy)-1,8,8-trimethyl-6H-cyclopentacyclooctane (104070-42-0) → (1α,6aβ,7aβ)-(+/-)-decahydro-5,5,7-trimethyl-3-(phenylmethoxy)cyclopenta<6,7>cyclooct<1,2-b>oxirene (90414-06-5) + (1R,3S,9R,10S)-5-Benzyloxy-7,7,10-trimethyl-2-oxa-tricyclo[7.3.0.01,3]dodecane (90414-06-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -30 - -10 ℃; for 1h; Title compound not separated from byproducts;

DOI:10.1021/ja00280a035

Reference yield:

(1β,9aβ)-(+/-)-1,2,3,5,7,8,9,9a-octahydro-6-(phenylmethoxy)-1,8,8-trimethyl-6H-cyclopentacyclooctane (104070-42-0) → (1α,6aβ,7aβ)-(+/-)-decahydro-5,5,7-trimethyl-3-(phenylmethoxy)cyclopenta<6,7>cyclooct<1,2-b>oxirene (90414-06-5) + (1R,3S,9R,10S)-5-Benzyloxy-7,7,10-trimethyl-2-oxa-tricyclo[7.3.0.01,3]dodecane (90414-06-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -30 - -10 ℃; for 1h; Title compound not separated from byproducts;

DOI:10.1021/ja00280a035

Reference yield:

(1β,2β,5β)-(+/-)-5-ethenyl-2-methylbicyclo<3.2.0>heptan-2-one (113472-65-4) → (1R,3S,9R,10S)-5-Benzyloxy-7,7,10-trimethyl-2-oxa-tricyclo[7.3.0.01,3]dodecane (90414-06-5)

Guidance literature:

Multi-step reaction with 8 steps

1: tetrahydrofuran / 0.2 h / -30 °C

2: 3 h / Heating

3: 94 percent / diethyl ether / 0.53 h / -78 °C

4: 78 percent / Celite, pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

5: 73 percent / CuBr-Me₂S complex / diethyl ether / 0.33 h / Ambient temperature

6: lithium aluminum hydride / diethyl ether / 0.25 h / -78 °C

7: 1.) potassium hydride, 2.) tetrabutylammonium iodide / 1.) THF, 15 min., room temp., 2.) room temp., 4 h.

8: MCPBA / CH₂Cl₂ / 1 h / -30 - -10 °C

With lithium aluminium tetrahydride; Celite; tetra-(n-butyl)ammonium iodide; potassium hydride; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja00280a035

upstream raw materials:

(1β,9aβ)-(+/-)-1,2,3,5,7,8,9,9a-octahydro-6-(phenylmethoxy)-1,8,8-trimethyl-6H-cyclopentacyclooctane

(1β,2β,5β)-(+/-)-5-ethenyl-2-methylbicyclo<3.2.0>heptan-2-one

1-methoxy-5-methyl-6-hepten-2-one

2-methoxy-4-methyl-2-cyclohexen-1-ol

Downstream raw materials:

(1β,3aα,9aβ)-(+/-)-decahydro-1,8,8-trimethyl-6-(phenylmethoxy)-3aH-cyclopentacyclooctan-3a-ol

(1β,3aβ,9aβ)-(+/-)-decahydro-1,8,8-trimethyl-6-(phenylmethoxy)-3aH-cyclopentacyclooctan-3a-ol

(1β,3aα,9aβ)-(+/-)-decahydro-1,8,8-trimethyl-3a-<<2-(trimethylsilyl)ethoxy>methoxy>-6-(phenylmethoxy)-3aH-cyclopentacyclooctane

(+/-)-Dactylol