Toluene-4-sulfonic acid (7R,8S,9S,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (7R,8S,9S,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-ylmethyl ester
• CAS No.: 133152-39-3
• Molecular Formula: C₃₃H₄₈O₅SSi
• Molecular Weight: 584.893

Synonyms:Toluene-4-sulfonic acid (7R,8S,9S,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (7R,8S,9S,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-ylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (7R,8S,9S,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-ylmethyl ester

There total 3 articles about Toluene-4-sulfonic acid (7R,8S,9S,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-ylmethyl 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: 95.0%

[(7R,8S,9S,13S,14S,17S)-17-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl]-methanol (133152-36-0) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (7R,8S,9S,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-ylmethyl ester (133152-39-3)

Guidance literature:

With pyridine; In chloroform; at 22 ℃; for 48h;

DOI:10.1016/S0040-4039(00)74873-8

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 (7R,8S,9S,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-ylmethyl ester (133152-39-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 56 percent / H₂ / Pd-C / ethyl acetate / Ambient temperature

2: 95 percent / pyridine / CHCl₃ / 48 h / 22 °C

With pyridine; hydrogen; palladium on activated charcoal; In chloroform; ethyl acetate;

DOI:10.1016/S0040-4039(00)74873-8

Reference yield:

[(7R,9R,13S,17S)-17-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-7,9,11,12,13,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-7-yl]-methanol (133152-37-1) → Toluene-4-sulfonic acid (7R,8S,9S,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-ylmethyl ester (133152-39-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / H₂ / Pd-C / ethyl acetate / Ambient temperature

2: 95 percent / pyridine / CHCl₃ / 48 h / 22 °C

With pyridine; hydrogen; palladium on activated charcoal; In chloroform; ethyl acetate;

DOI:10.1016/S0040-4039(00)74873-8

upstream raw materials:

[(7R,8S,9S,13S,14S,17S)-17-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl]-methanol

p-toluenesulfonyl chloride

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

[(7R,9R,13S,17S)-17-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-13-methyl-7,9,11,12,13,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-7-yl]-methanol

Downstream raw materials:

3-methoxy-7α-methyl-8α-estra-1,3,5(10)-trien-17β-ol

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