[4S-(4β,5β,9α,10β,13β,17β)]-17-(tert-butyldimethylsilanyloxy)-4-(tert-butyldiphenylsilanyloxy)-13-methyl-1,7-dioxo-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

Base Information

• Chemical Name: [4S-(4β,5β,9α,10β,13β,17β)]-17-(tert-butyldimethylsilanyloxy)-4-(tert-butyldiphenylsilanyloxy)-13-methyl-1,7-dioxo-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester
• CAS No.: 502761-43-5
• Molecular Formula: C₄₂H₅₈O₆Si₂
• Molecular Weight: 715.09

Synonyms:[4S-(4β,5β,9α,10β,13β,17β)]-17-(tert-butyldimethylsilanyloxy)-4-(tert-butyldiphenylsilanyloxy)-13-methyl-1,7-dioxo-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

Chemical Property of [4S-(4β,5β,9α,10β,13β,17β)]-17-(tert-butyldimethylsilanyloxy)-4-(tert-butyldiphenylsilanyloxy)-13-methyl-1,7-dioxo-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of [4S-(4β,5β,9α,10β,13β,17β)]-17-(tert-butyldimethylsilanyloxy)-4-(tert-butyldiphenylsilanyloxy)-13-methyl-1,7-dioxo-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

There total 7 articles about [4S-(4β,5β,9α,10β,13β,17β)]-17-(tert-butyldimethylsilanyloxy)-4-(tert-butyldiphenylsilanyloxy)-13-methyl-1,7-dioxo-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl 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: 17.0%

(4S)-4-t-butyldiphenylsilyloxy-2-carbomethoxycyclohex-2-en-1-one (415928-19-7) + [1S-(1β,7aβ)]-3-[1-(tert-butyldimethylsilanyloxy)-7a-methyl-2,6,7,7a-tetrahydro-1H-inden-4-yl]-3-oxopropionic acid allyl ester (502764-67-2) → [4S-(4β,5α,9β,10α,13β,17β)]-17-(tert-butyldimethylsilanyloxy)-4-(tert-butyldiphenylsilanyloxy)-13-methyl-1,7-dioxo-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester + [4S-(4β,5β,9α,10β,13β,17β)]-17-(tert-butyldimethylsilanyloxy)-4-(tert-butyldiphenylsilanyloxy)-13-methyl-1,7-dioxo-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester (502761-43-5)

Guidance literature:

(4S)-4-t-butyldiphenylsilyloxy-2-carbomethoxycyclohex-2-en-1-one; [1S-(1β,7aβ)]-3-[1-(tert-butyldimethylsilanyloxy)-7a-methyl-2,6,7,7a-tetrahydro-1H-inden-4-yl]-3-oxopropionic acid allyl ester; With caesium carbonate; In dichloromethane; at 20 ℃; for 16h;

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/jo026676p

Reference yield:

<1S-(1α,7aα)>-1,2,5,6,7,7a-Hexahydro-1-<(tert-butyldimethylsilyl)oxy>-7a-methyl-4H-inden-4-one (140659-36-5) → [4S-(4β,5β,9α,10β,13β,17β)]-17-(tert-butyldimethylsilanyloxy)-4-(tert-butyldiphenylsilanyloxy)-13-methyl-1,7-dioxo-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester (502761-43-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 2 h / -78 °C

1.2: 73 percent / tetrahydrofuran / 3 h / -30 °C

2.1: 60 percent / K₂CO₃ / bis(triphenylphosphine)palladium(II) chloride / dimethylformamide / 40 h / 20 °C / 760 Torr

3.1: 86 percent / diisobutylaluminum hydride / CH₂Cl₂ / 2 h / -78 °C

4.1: 86 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

5.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 0.17 h / -78 °C

5.2: 89 percent / tetrahydrofuran / 0.5 h / -78 °C

6.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

7.1: cesium carbonate / CH₂Cl₂ / 16 h / 20 °C

7.2: 17 percent / morpholine / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 3 h / 20 °C

With n-butyllithium; diisobutylaluminium hydride; potassium carbonate; caesium carbonate; Dess-Martin periodane; diisopropylamine; bis(triphenylphosphine)palladium(II)-chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 4.1: Dess-Martin oxidation / 6.1: Dess-Martin oxidation;

DOI:10.1021/jo026676p

Reference yield:

trifluoromethanesulfonic acid [1S-(1β,7aβ)]-1-(tert-butyldimethylsilanyloxy)-7a-methyl-2,6,7,7a-tetrahydro-1H-inden-4-yl ester (502761-50-4) → [4S-(4β,5β,9α,10β,13β,17β)]-17-(tert-butyldimethylsilanyloxy)-4-(tert-butyldiphenylsilanyloxy)-13-methyl-1,7-dioxo-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester (502761-43-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 60 percent / K₂CO₃ / bis(triphenylphosphine)palladium(II) chloride / dimethylformamide / 40 h / 20 °C / 760 Torr

2.1: 86 percent / diisobutylaluminum hydride / CH₂Cl₂ / 2 h / -78 °C

3.1: 86 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

4.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 0.17 h / -78 °C

4.2: 89 percent / tetrahydrofuran / 0.5 h / -78 °C

5.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

6.1: cesium carbonate / CH₂Cl₂ / 16 h / 20 °C

6.2: 17 percent / morpholine / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 3 h / 20 °C

With n-butyllithium; diisobutylaluminium hydride; potassium carbonate; caesium carbonate; Dess-Martin periodane; diisopropylamine; bis(triphenylphosphine)palladium(II)-chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3.1: Dess-Martin oxidation / 5.1: Dess-Martin oxidation;

DOI:10.1021/jo026676p

upstream raw materials:

(4S)-4-t-butyldiphenylsilyloxy-2-carbomethoxycyclohex-2-en-1-one

[1S-(1β,7aβ)]-3-[1-(tert-butyldimethylsilanyloxy)-7a-methyl-2,6,7,7a-tetrahydro-1H-inden-4-yl]-3-oxopropionic acid allyl ester

<1S-(1α,7aα)>-1,2,5,6,7,7a-Hexahydro-1-<(tert-butyldimethylsilyl)oxy>-7a-methyl-4H-inden-4-one

[1S-(1β,7aβ)]-1-(tert-butyldimethylsilanyloxy)-7a-methyl-2,6,7,7a-tetrahydro-1H-indene-4-carbaldehyde

Downstream raw materials:

[4S-(4β,5β,9α,10β,13β,17β)]-4-(tert-butyldiphenylsilanyloxy)-13-methyl-17-(4-nitrobenzoyloxy)-1-oxo-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

[4S-(4β,5β,9α,10β,13β,17β)]-4-(tert-butyldiphenylsilanyloxy)-17-hydroxy-13-methyl-1-oxo-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

[4S-(4β,5β,9α,10β,13β,17β)]-4-hydroxy-13-methyl-17-(4-nitrobenzoyloxy)-1-oxo-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

[4S-(4β,5β,9α,10β,13β,17β)]-4-(tert-butyldiphenylsilanyloxy)-17-hydroxy-13-methyl-1,7-dioxo-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

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