Toluene-4-sulfonic acid (S)-2-[(3S,5S,8R,9S,10S,13R,14S,15R,17R)-3-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-propyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (S)-2-[(3S,5S,8R,9S,10S,13R,14S,15R,17R)-3-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-propyl ester
CAS No.:224448-11-7
Molecular Formula:C₃₅H₅₈O₅SSi
Molecular Weight:618.994
Hs Code.:

Toluene-4-sulfonic acid (S)-2-[(3S,5S,8R,9S,10S,13R,14S,15R,17R)-3-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-propyl ester

Synonyms:Toluene-4-sulfonic acid (S)-2-[(3S,5S,8R,9S,10S,13R,14S,15R,17R)-3-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-propyl ester

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Chemical Property of Toluene-4-sulfonic acid (S)-2-[(3S,5S,8R,9S,10S,13R,14S,15R,17R)-3-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-propyl ester

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Technology Process of Toluene-4-sulfonic acid (S)-2-[(3S,5S,8R,9S,10S,13R,14S,15R,17R)-3-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-propyl ester

There total 11 articles about Toluene-4-sulfonic acid (S)-2-[(3S,5S,8R,9S,10S,13R,14S,15R,17R)-3-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-10,13-dimethyl-hexadecahydro-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: 90.0%

: 98-59-9
p-toluenesulfonyl chloride

: 224448-10-6
3β-<(tert-butyldimethylsilyl)oxy>-23-nor-5α-cholane-15β,22-diol

: 224448-11-7
Toluene-4-sulfonic acid (S)-2-[(3S,5S,8R,9S,10S,13R,14S,15R,17R)-3-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-propyl ester

Guidance literature:: With pyridine; at 0 ℃; for 24h;
DOI:10.1021/jo982319w

Reference yield:

: 481-29-8
Epiandrosterone

: 224448-11-7
Toluene-4-sulfonic acid (S)-2-[(3S,5S,8R,9S,10S,13R,14S,15R,17R)-3-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-propyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) LDA, 2.) Et₃N / 1.) THF, -78 deg C, 15 min, 2.) room temperature, 25 min

2: Pd(OAc)2 / CH₂Cl₂; acetonitrile / 3 h / 35 - 40 °C

3: 1.) BuLi / 1.) THF, hexane, -20 deg C, 1.5 h, 2.) THF, room temperature, 20 h

4: 80 percent / H₂SO₄ / tetrahydrofuran; H₂O / Ambient temperature

5: 62 percent / Tl(NO₃)3*3H₂O / methanol; tetrahydrofuran / 0.17 h / Ambient temperature

6: 90 percent / pyridine / CH₂Cl₂

7: 97 percent / H₂ / Rh/alumina / ethanol / 3 h / Ambient temperature

8: 1.) BuLi / 1.) THF, hexane, 0 deg C, 15 min; room temperature, 20 min, 2.) THF, reflux, 3 h

9: 1.) borane-dimethyl sulfide complex, cyclohexene, 2.) NaOH, H₂O₂ / 1.) THF, 0 deg C, 24 h, 2.) EtOH, room temperature, 24 h

10: 90 percent / pyridine / 24 h / 0 °C

With pyridine; palladium diacetate; sodium hydroxide; n-butyllithium; dimethylsulfide borane complex; sulfuric acid; hydrogen; dihydrogen peroxide; triethylamine; thallium(III) nitrate; lithium diisopropyl amide; cyclohexene; Rh/Al₂O₃; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo982319w

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 224448-11-7
Toluene-4-sulfonic acid (S)-2-[(3S,5S,8R,9S,10S,13R,14S,15R,17R)-3-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-propyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / pyridine / CH₂Cl₂

2: 97 percent / H₂ / Rh/alumina / ethanol / 3 h / Ambient temperature

3: 1.) BuLi / 1.) THF, hexane, 0 deg C, 15 min; room temperature, 20 min, 2.) THF, reflux, 3 h

4: 1.) borane-dimethyl sulfide complex, cyclohexene, 2.) NaOH, H₂O₂ / 1.) THF, 0 deg C, 24 h, 2.) EtOH, room temperature, 24 h

5: 90 percent / pyridine / 24 h / 0 °C

With pyridine; sodium hydroxide; n-butyllithium; dimethylsulfide borane complex; hydrogen; dihydrogen peroxide; cyclohexene; Rh/Al₂O₃; In ethanol; dichloromethane;
DOI:10.1021/jo982319w