(4S,5R,8S,9R,10R,13S,14S,17S)-4-(tert-Butyl-diphenyl-silanyloxy)-17-methoxymethoxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

Base Information

Chemical Name:(4S,5R,8S,9R,10R,13S,14S,17S)-4-(tert-Butyl-diphenyl-silanyloxy)-17-methoxymethoxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester
CAS No.:415928-20-0
Molecular Formula:C₃₈H₅₀O₇Si
Molecular Weight:646.896
Hs Code.:

(4S,5R,8S,9R,10R,13S,14S,17S)-4-(tert-Butyl-diphenyl-silanyloxy)-17-methoxymethoxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

Synonyms:(4S,5R,8S,9R,10R,13S,14S,17S)-4-(tert-Butyl-diphenyl-silanyloxy)-17-methoxymethoxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

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Chemical Property of (4S,5R,8S,9R,10R,13S,14S,17S)-4-(tert-Butyl-diphenyl-silanyloxy)-17-methoxymethoxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

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Technology Process of (4S,5R,8S,9R,10R,13S,14S,17S)-4-(tert-Butyl-diphenyl-silanyloxy)-17-methoxymethoxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

There total 11 articles about (4S,5R,8S,9R,10R,13S,14S,17S)-4-(tert-Butyl-diphenyl-silanyloxy)-17-methoxymethoxy-13-methyl-1,7-dioxo-hexadecahydro-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:

: 415928-12-0
3-((1S,3aR,7aS)-1-Methoxymethoxy-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl)-3-oxo-propionic acid allyl ester

: 415928-19-7
(4S)-4-t-butyldiphenylsilyloxy-2-carbomethoxycyclohex-2-en-1-one

: (4S,5R,8R,9R,10R,13S,14S,17S)-4-(tert-Butyl-diphenyl-silanyloxy)-17-methoxymethoxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

: 415928-20-0
(4S,5R,8S,9R,10R,13S,14S,17S)-4-(tert-Butyl-diphenyl-silanyloxy)-17-methoxymethoxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

Guidance literature:: 3-((1S,3aR,7aS)-1-Methoxymethoxy-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl)-3-oxo-propionic acid allyl ester; (4S)-4-t-butyldiphenylsilyloxy-2-carbomethoxycyclohex-2-en-1-one; With caesium carbonate; In dichloromethane; at 20 ℃; for 18h;

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 3h; Further stages.;
DOI:10.1021/ol017274r

Reference yield:

: 17553-86-5
(S)-Halos-Parish ketone

: 415928-20-0
(4S,5R,8S,9R,10R,13S,14S,17S)-4-(tert-Butyl-diphenyl-silanyloxy)-17-methoxymethoxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 90 percent / NaBH₄ / CH₂Cl₂; methanol / -78 °C

2.1: 61 percent / (i-Pr)2NEt / CH₂Cl₂ / 18 h / 20 °C

3.1: dimethylformamide / 3 h / 125 °C

4.1: diethyl ether / 0 °C

5.1: H₂ / Pd/BaSO₄ / ethanol / 18 h / 20 °C

6.1: NaBH₄ / methanol / 2 h / -78 °C

7.1: 93 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

8.1: 65 percent / DIBAL / diethyl ether; CH₂Cl₂ / 2 h / -78 °C

9.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

10.1: 97 percent / sodium iodate; pyridine / dimethylformamide / 2 h / 100 °C

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

11.2: 88 percent / tetrahydrofuran / 0.25 h / -78 °C

12.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

13.1: Cs₂CO₃ / CH₂Cl₂ / 18 h / 20 °C

13.2: morpholine / Pd(PPh₃)4 / tetrahydrofuran / 3 h / 20 °C

With pyridine; sodium tetrahydroborate; n-butyllithium; sodium iodate; hydrogen; diisobutylaluminium hydride; caesium carbonate; Dess-Martin periodane; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; 9.1: Dess-Martin oxidation reaction / 12.1: Dess-Martin oxidation reaction;
DOI:10.1021/ol017274r

Reference yield:

: 16271-49-1
(1S,7aS)-1-hydroxy-7a-methyl-2,3,7,7a-tetrahydro-1H-inden-5(6H)-one

: 415928-20-0
(4S,5R,8S,9R,10R,13S,14S,17S)-4-(tert-Butyl-diphenyl-silanyloxy)-17-methoxymethoxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: 61 percent / (i-Pr)2NEt / CH₂Cl₂ / 18 h / 20 °C

2.1: dimethylformamide / 3 h / 125 °C

3.1: diethyl ether / 0 °C

4.1: H₂ / Pd/BaSO₄ / ethanol / 18 h / 20 °C

5.1: NaBH₄ / methanol / 2 h / -78 °C

6.1: 93 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

7.1: 65 percent / DIBAL / diethyl ether; CH₂Cl₂ / 2 h / -78 °C

8.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

9.1: 97 percent / sodium iodate; pyridine / dimethylformamide / 2 h / 100 °C

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

10.2: 88 percent / tetrahydrofuran / 0.25 h / -78 °C

11.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

12.1: Cs₂CO₃ / CH₂Cl₂ / 18 h / 20 °C

12.2: morpholine / Pd(PPh₃)4 / tetrahydrofuran / 3 h / 20 °C

With pyridine; sodium tetrahydroborate; n-butyllithium; sodium iodate; hydrogen; diisobutylaluminium hydride; caesium carbonate; Dess-Martin periodane; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; 8.1: Dess-Martin oxidation reaction / 11.1: Dess-Martin oxidation reaction;
DOI:10.1021/ol017274r