1-[(3S,5R,8R,9R,10R,13R,14R,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone

Base Information

• Chemical Name: 1-[(3S,5R,8R,9R,10R,13R,14R,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone
• CAS No.: 241816-36-4
• Molecular Formula: C₄₀H₅₈O₂Si
• Molecular Weight: 598.985
• Mol file: 241816-36-4.mol

Synonyms:1-[(3S,5R,8R,9R,10R,13R,14R,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone

Chemical Property of 1-[(3S,5R,8R,9R,10R,13R,14R,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(3S,5R,8R,9R,10R,13R,14R,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone

There total 6 articles about 1-[(3S,5R,8R,9R,10R,13R,14R,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone 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:

20-ξ(2)-Hydroxy-3-oxo-dammaren-(24); Dipterocarpol (19222-66-3) → 1-[(3S,5R,8R,9R,10R,13R,14R,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone (241816-36-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 24 percent / NaBH₄ / propan-2-ol / 3.5 h / Ambient temperature

2: 95 percent / H₂ / Pd/C / ethanol / 3 h

3: 2.) O₃, Ph₃P / 1.) DMSO, 190 deg C, 3 h, 2.) CH₂Cl₂, MeOH

4: 87 percent / imidazole / acetonitrile / 12 h / 60 °C

5: 72 percent / pTsOH / 7.5 h / Heating

6: 1.) MeLi, 2.) methyl salicylate / 1.) Et₂O, 0 deg C, 30 min, 2.) Et₂O, -78 deg C, 40 min

With 1H-imidazole; sodium tetrahydroborate; methyllithium; hydrogen; toluene-4-sulfonic acid; ozone; triphenylphosphine; methyl salicylate; palladium on activated charcoal; In ethanol; isopropyl alcohol; acetonitrile;

DOI:10.1016/S0960-894X(99)00220-6

Reference yield:

'Dammarendiol' (19132-83-3) → 1-[(3S,5R,8R,9R,10R,13R,14R,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone (241816-36-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / H₂ / Pd/C / ethanol / 3 h

2: 2.) O₃, Ph₃P / 1.) DMSO, 190 deg C, 3 h, 2.) CH₂Cl₂, MeOH

3: 87 percent / imidazole / acetonitrile / 12 h / 60 °C

4: 72 percent / pTsOH / 7.5 h / Heating

5: 1.) MeLi, 2.) methyl salicylate / 1.) Et₂O, 0 deg C, 30 min, 2.) Et₂O, -78 deg C, 40 min

With 1H-imidazole; methyllithium; hydrogen; toluene-4-sulfonic acid; ozone; triphenylphosphine; methyl salicylate; palladium on activated charcoal; In ethanol; acetonitrile;

DOI:10.1016/S0960-894X(99)00220-6

Reference yield:

3β-hydroxy-22,23,24,25,26,27-hexanordammaran-20-one (3819-21-4) → 1-[(3S,5R,8R,9R,10R,13R,14R,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone (241816-36-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / imidazole / acetonitrile / 12 h / 60 °C

2: 72 percent / pTsOH / 7.5 h / Heating

3: 1.) MeLi, 2.) methyl salicylate / 1.) Et₂O, 0 deg C, 30 min, 2.) Et₂O, -78 deg C, 40 min

With 1H-imidazole; methyllithium; toluene-4-sulfonic acid; methyl salicylate; In acetonitrile;

DOI:10.1016/S0960-894X(99)00220-6

upstream raw materials:

20-ξ(2)-Hydroxy-3-oxo-dammaren-(24); Dipterocarpol

'Dammarendiol'

3β-hydroxy-22,23,24,25,26,27-hexanordammaran-20-one

1-[(3S,5R,8R,9R,10R,13R,14R,17S)-3-(tert-Butyl-diphenyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone

Downstream raw materials:

Trifluoro-methanesulfonic acid 1-[(3S,5R,8R,9R,10R,13R,14R,17R)-3-(tert-butyl-diphenyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-vinyl ester

C₅₅H₈₂N₂O₃SSi