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

Base Information

• Chemical Name: 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
• CAS No.: 241816-37-5
• Molecular Formula: C₄₁H₅₇F₃O₄SSi
• Molecular Weight: 731.048
• Mol file: 241816-37-5.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 7 articles about 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 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: 67.0%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 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) → 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 (241816-37-5)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at -78 - 0 ℃;

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

Reference yield:

20-ξ(2)-Hydroxy-3-oxo-dammaren-(24); Dipterocarpol (19222-66-3) → 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 (241816-37-5)

Guidance literature:

Multi-step reaction with 7 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

7: 67 percent / KN(SiMe₃)2 / tetrahydrofuran / -78 - 0 °C

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

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

Reference yield:

'Dammarendiol' (19132-83-3) → 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 (241816-37-5)

Guidance literature:

Multi-step reaction with 6 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

6: 67 percent / KN(SiMe₃)2 / tetrahydrofuran / -78 - 0 °C

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

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

upstream raw materials:

N,N-phenylbistrifluoromethane-sulfonimide

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

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

'Dammarendiol'