(7R,10E,12aS,13S,16aR)-7-[(1R)-1-(benzyloxy)ethyl]-2,3,6,7,12a,13,14,15,16,16a-decahydro-13,16a-dimethyl-5H-1,4,8-benzotrioxacyclotetradecine-5,9(12H)-dione

Base Information

• Chemical Name: (7R,10E,12aS,13S,16aR)-7-[(1R)-1-(benzyloxy)ethyl]-2,3,6,7,12a,13,14,15,16,16a-decahydro-13,16a-dimethyl-5H-1,4,8-benzotrioxacyclotetradecine-5,9(12H)-dione
• CAS No.: 620616-19-5
• Molecular Formula: C₂₆H₃₆O₆
• Molecular Weight: 444.568
• Mol file: 620616-19-5.mol

Synonyms:

Chemical Property of (7R,10E,12aS,13S,16aR)-7-[(1R)-1-(benzyloxy)ethyl]-2,3,6,7,12a,13,14,15,16,16a-decahydro-13,16a-dimethyl-5H-1,4,8-benzotrioxacyclotetradecine-5,9(12H)-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7R,10E,12aS,13S,16aR)-7-[(1R)-1-(benzyloxy)ethyl]-2,3,6,7,12a,13,14,15,16,16a-decahydro-13,16a-dimethyl-5H-1,4,8-benzotrioxacyclotetradecine-5,9(12H)-dione

There total 11 articles about (7R,10E,12aS,13S,16aR)-7-[(1R)-1-(benzyloxy)ethyl]-2,3,6,7,12a,13,14,15,16,16a-decahydro-13,16a-dimethyl-5H-1,4,8-benzotrioxacyclotetradecine-5,9(12H)-dione 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:

trans-chrotonyl chloride (625-35-4,3488-22-0,10487-71-5) + 2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate (622405-00-9) → (7R,10E,12aS,13S,16aR)-7-[(1R)-1-(benzyloxy)ethyl]-2,3,6,7,12a,13,14,15,16,16a-decahydro-13,16a-dimethyl-5H-1,4,8-benzotrioxacyclotetradecine-5,9(12H)-dione (620616-19-5) + (7R,10E,12aR,13R,16aS)-7-[(1R)-1-(benzyloxy)ethyl]-2,3,6,7,12a,13,14,15,16,16a-decahydro-13,16a-dimethyl-5H-1,4,8-benzotrioxacyclotetradecine-5,9(12H)-dione (620616-20-8)

Guidance literature:

trans-chrotonyl chloride; 2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate; With triethylamine; In diethyl ether; at 0 - 20 ℃;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In diethyl ether; for 13.5h;

With ruthenium; In dichloromethane; for 24h; Heating;

DOI:10.1002/hlca.200390151

Reference yield:

2-allyl-cyclohex-2-enone (38019-50-0) → (7R,10E,12aS,13S,16aR)-7-[(1R)-1-(benzyloxy)ethyl]-2,3,6,7,12a,13,14,15,16,16a-decahydro-13,16a-dimethyl-5H-1,4,8-benzotrioxacyclotetradecine-5,9(12H)-dione (620616-19-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: CuI / diethyl ether; hexane / 1 h / -78 °C

1.2: 80 percent / methyl 2-hydroxybenzoate / diethyl ether; hexane / -78 - 20 °C

2.1: 87 percent / trimethylsilyl triflate / CH₂Cl₂ / 12 h / -78 - 20 °C

3.1: 90 percent / hexane; CH₂Cl₂ / 12 h / -78 - 0 °C

4.1: 79 percent / DMAP; Et₃N; 2,4,6-trichlorobenzoyl chloride / toluene / 20 h / 0 °C

5.1: 66 percent / Bu₄NF / tetrahydrofuran / 0 - 20 °C

6.1: Et₃N / diethyl ether / 0 - 20 °C

6.2: DBU / diethyl ether / 13.5 h

6.3: Ru complex / CH₂Cl₂ / 24 h / Heating

With dmap; copper(l) iodide; trimethylsilyl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 4.1: Yamaguchi activation;

DOI:10.1002/hlca.200390151

Reference yield:

trans-3-Methyl-2-(2-propenyl)cyclohexanone (61674-94-0,795275-74-0) → (7R,10E,12aS,13S,16aR)-7-[(1R)-1-(benzyloxy)ethyl]-2,3,6,7,12a,13,14,15,16,16a-decahydro-13,16a-dimethyl-5H-1,4,8-benzotrioxacyclotetradecine-5,9(12H)-dione (620616-19-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 87 percent / trimethylsilyl triflate / CH₂Cl₂ / 12 h / -78 - 20 °C

2.1: 90 percent / hexane; CH₂Cl₂ / 12 h / -78 - 0 °C

3.1: 79 percent / DMAP; Et₃N; 2,4,6-trichlorobenzoyl chloride / toluene / 20 h / 0 °C

4.1: 66 percent / Bu₄NF / tetrahydrofuran / 0 - 20 °C

5.1: Et₃N / diethyl ether / 0 - 20 °C

5.2: DBU / diethyl ether / 13.5 h

5.3: Ru complex / CH₂Cl₂ / 24 h / Heating

With dmap; trimethylsilyl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 3.1: Yamaguchi activation;

DOI:10.1002/hlca.200390151

upstream raw materials:

trans-chrotonyl chloride

2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate

2-allyl-cyclohex-2-enone

trans-3-Methyl-2-(2-propenyl)cyclohexanone