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Technology Process of Toluene-4-sulfonic acid (S)-2-[(1S,3R,9S,10R,13R,14R,17R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propyl ester

Toluene-4-sulfonic acid (S)-2-[(1S,3R,9S,10R,13R,14R,17R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propyl ester

Base Information
  • Chemical Name:Toluene-4-sulfonic acid (S)-2-[(1S,3R,9S,10R,13R,14R,17R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propyl ester
  • CAS No.:126771-94-6
  • Molecular Formula:C41H68O5SSi2
  • Molecular Weight:729.225
  • Hs Code.:
Toluene-4-sulfonic acid (S)-2-[(1S,3R,9S,10R,13R,14R,17R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propyl ester

Synonyms:Toluene-4-sulfonic acid (S)-2-[(1S,3R,9S,10R,13R,14R,17R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propyl ester

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Chemical Property of Toluene-4-sulfonic acid (S)-2-[(1S,3R,9S,10R,13R,14R,17R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propyl ester
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Technology Process of Toluene-4-sulfonic acid (S)-2-[(1S,3R,9S,10R,13R,14R,17R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propyl ester

There total 9 articles about Toluene-4-sulfonic acid (S)-2-[(1S,3R,9S,10R,13R,14R,17R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-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:

1α,3β-dihydroxy-androst-5-en-17-one
20998-18-9

1α,3β-dihydroxy-androst-5-en-17-one

Toluene-4-sulfonic acid (S)-2-[(1S,3R,9S,10R,13R,14R,17R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propyl ester
126771-94-6

Toluene-4-sulfonic acid (S)-2-[(1S,3R,9S,10R,13R,14R,17R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propyl ester

Guidance literature:
Multi-step reaction with 8 steps
1: 89 percent / imidazole / dimethylformamide / 0.5 h / Ambient temperature
2: 98 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / Ambient temperature
3: 100 percent / tert-BuOK / tetrahydrofuran / 4 h / Heating
4: 89 percent / BF3*Et2O / CH2Cl2 / 0.08 h / Ambient temperature
5: 95 percent / H2 / 5percent Pt/C / ethanol / Ambient temperature
6: 1.) N-bromosuccinimide (NBS), NaHCO3, 2.) n-Bu4NBr / 1.) n-hexane, reflux, 1 h, 2.) THF, 0 deg C, 15 min
7: n-Bu4NF / tetrahydrofuran / 3.5 h / 0 °C
8: 4-dimethylaminopyridine (DMAP) / CH2Cl2 / Ambient temperature
With 1H-imidazole; 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; sodium hydrogencarbonate; platinum on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.40.1120

Reference yield:

t-butyldimethylsiyl triflate
69739-34-0

t-butyldimethylsiyl triflate

Toluene-4-sulfonic acid (S)-2-[(1S,3R,9S,10R,13R,14R,17R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propyl ester
126771-94-6

Toluene-4-sulfonic acid (S)-2-[(1S,3R,9S,10R,13R,14R,17R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propyl ester

Guidance literature:
Multi-step reaction with 7 steps
1: 98 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / Ambient temperature
2: 100 percent / tert-BuOK / tetrahydrofuran / 4 h / Heating
3: 89 percent / BF3*Et2O / CH2Cl2 / 0.08 h / Ambient temperature
4: 95 percent / H2 / 5percent Pt/C / ethanol / Ambient temperature
5: 1.) N-bromosuccinimide (NBS), NaHCO3, 2.) n-Bu4NBr / 1.) n-hexane, reflux, 1 h, 2.) THF, 0 deg C, 15 min
6: n-Bu4NF / tetrahydrofuran / 3.5 h / 0 °C
7: 4-dimethylaminopyridine (DMAP) / CH2Cl2 / Ambient temperature
With 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; sodium hydrogencarbonate; platinum on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1248/cpb.40.1120

Reference yield:

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Toluene-4-sulfonic acid (S)-2-[(1S,3R,9S,10R,13R,14R,17R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propyl ester
126771-94-6

Toluene-4-sulfonic acid (S)-2-[(1S,3R,9S,10R,13R,14R,17R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propyl ester

Guidance literature:
Multi-step reaction with 8 steps
1: 89 percent / imidazole / dimethylformamide / 0.5 h / Ambient temperature
2: 98 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / Ambient temperature
3: 100 percent / tert-BuOK / tetrahydrofuran / 4 h / Heating
4: 89 percent / BF3*Et2O / CH2Cl2 / 0.08 h / Ambient temperature
5: 95 percent / H2 / 5percent Pt/C / ethanol / Ambient temperature
6: 1.) N-bromosuccinimide (NBS), NaHCO3, 2.) n-Bu4NBr / 1.) n-hexane, reflux, 1 h, 2.) THF, 0 deg C, 15 min
7: n-Bu4NF / tetrahydrofuran / 3.5 h / 0 °C
8: 4-dimethylaminopyridine (DMAP) / CH2Cl2 / Ambient temperature
With 1H-imidazole; 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; sodium hydrogencarbonate; platinum on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.40.1120
upstream raw materials:

t-butyldimethylsiyl triflate

1α,3β-dihydroxy-androst-5-en-17-one

tert-butyldimethylsilyl chloride

1α,3β-bis<(tert-butyldimethylsilyl)oxy>-23,24-bisnorchol-5-en-22-ol

Downstream raw materials:

24F2-1,25(OH)2-D3

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