Toluene-4-sulfonic acid 3-[(9R,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-6,11,12,13,14,15,16,17-octahydro-cyclopenta[a]phenanthren-9-yl]-propyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid 3-[(9R,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-6,11,12,13,14,15,16,17-octahydro-cyclopenta[a]phenanthren-9-yl]-propyl ester
• CAS No.: 182241-57-2
• Molecular Formula: C₃₅H₅₀O₅SSi
• Molecular Weight: 610.931
• Mol file: 182241-57-2.mol

Synonyms:Toluene-4-sulfonic acid 3-[(9R,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-6,11,12,13,14,15,16,17-octahydro-cyclopenta[a]phenanthren-9-yl]-propyl ester

Chemical Property of Toluene-4-sulfonic acid 3-[(9R,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-6,11,12,13,14,15,16,17-octahydro-cyclopenta[a]phenanthren-9-yl]-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid 3-[(9R,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-6,11,12,13,14,15,16,17-octahydro-cyclopenta[a]phenanthren-9-yl]-propyl ester

There total 6 articles about Toluene-4-sulfonic acid 3-[(9R,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-6,11,12,13,14,15,16,17-octahydro-cyclopenta[a]phenanthren-9-yl]-propyl 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: 84.0%

p-toluenesulfonyl chloride (98-59-9) + 3-[(9R,13S,14S,17S)-17-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-6,11,12,13,14,15,16,17-octahydro-cyclopenta[a]phenanthren-9-yl]-propan-1-ol (182241-56-1) → Toluene-4-sulfonic acid 3-[(9R,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-6,11,12,13,14,15,16,17-octahydro-cyclopenta[a]phenanthren-9-yl]-propyl ester (182241-57-2)

Guidance literature:

With pyridine; In chloroform; at 0 ℃; for 24h;

DOI:10.1016/0040-4039(96)01342-1

Reference yield:

(7α,17β)-17-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxyestra-1,3,5(10),8-tetraene-7-methanol (133152-35-9) → Toluene-4-sulfonic acid 3-[(9R,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-6,11,12,13,14,15,16,17-octahydro-cyclopenta[a]phenanthren-9-yl]-propyl ester (182241-57-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / DMSO, pyridine*SO₃, Et₃N / 22 °C

2: tetrahydrofuran / -78 °C

3: 83 percent / KH, 18-crown-6 / tetrahydrofuran / 2 h / 0 °C

4: 93 percent / NaBH₄ / methanol / 0 °C

5: 84 percent / pyridine / CHCl₃ / 24 h / 0 °C

With pyridine; sodium tetrahydroborate; 18-crown-6 ether; sulfur trioxide pyridine complex; potassium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; chloroform;

DOI:10.1016/0040-4039(96)01342-1

Reference yield:

(7R,13S,14S,17S)-17-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-7,11,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene-7-carbaldehyde (182241-52-7) → Toluene-4-sulfonic acid 3-[(9R,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-6,11,12,13,14,15,16,17-octahydro-cyclopenta[a]phenanthren-9-yl]-propyl ester (182241-57-2)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / -78 °C

2: 83 percent / KH, 18-crown-6 / tetrahydrofuran / 2 h / 0 °C

3: 93 percent / NaBH₄ / methanol / 0 °C

4: 84 percent / pyridine / CHCl₃ / 24 h / 0 °C

With pyridine; sodium tetrahydroborate; 18-crown-6 ether; potassium hydride; In tetrahydrofuran; methanol; chloroform;

DOI:10.1016/0040-4039(96)01342-1

upstream raw materials:

p-toluenesulfonyl chloride

3-[(9R,13S,14S,17S)-17-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-6,11,12,13,14,15,16,17-octahydro-cyclopenta[a]phenanthren-9-yl]-propan-1-ol

(7α,17β)-17-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxyestra-1,3,5(10),8-tetraene-7-methanol

3-[(9R,13S,14S,17S)-17-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-6,11,12,13,14,15,16,17-octahydro-cyclopenta[a]phenanthren-9-yl]-propionaldehyde