(4S,5S,8R,9S,10R,11R,13R,14S,17S)-11-Acetoxy-4-(tert-butyl-diphenyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxymethyl)-14-hydroxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

Base Information

Chemical Name:(4S,5S,8R,9S,10R,11R,13R,14S,17S)-11-Acetoxy-4-(tert-butyl-diphenyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxymethyl)-14-hydroxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester
CAS No.:493021-08-2
Molecular Formula:C₅₅H₆₈O₉Si₂
Molecular Weight:929.311
Hs Code.:

(4S,5S,8R,9S,10R,11R,13R,14S,17S)-11-Acetoxy-4-(tert-butyl-diphenyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxymethyl)-14-hydroxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

Synonyms:(4S,5S,8R,9S,10R,11R,13R,14S,17S)-11-Acetoxy-4-(tert-butyl-diphenyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxymethyl)-14-hydroxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

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Chemical Property of (4S,5S,8R,9S,10R,11R,13R,14S,17S)-11-Acetoxy-4-(tert-butyl-diphenyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxymethyl)-14-hydroxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

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Technology Process of (4S,5S,8R,9S,10R,11R,13R,14S,17S)-11-Acetoxy-4-(tert-butyl-diphenyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxymethyl)-14-hydroxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

There total 17 articles about (4S,5S,8R,9S,10R,11R,13R,14S,17S)-11-Acetoxy-4-(tert-butyl-diphenyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxymethyl)-14-hydroxy-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: 71.0%

: 493021-14-0
(1S,4aS,5S,8aS)-5-{(R)-1-Acetoxy-2-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-5-oxo-cyclopentyl]-ethyl}-1-(tert-butyl-diphenyl-silanyloxy)-4,7-dioxo-octahydro-naphthalene-4a-carboxylic acid methyl ester

: 493021-08-2
(4S,5S,8R,9S,10R,11R,13R,14S,17S)-11-Acetoxy-4-(tert-butyl-diphenyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxymethyl)-14-hydroxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

Guidance literature:: With potassium bis(tetramethylsilyl)amide; In tetrahydrofuran; for 1.5h; Heating;
DOI:10.1021/ol027125o

Reference yield:

: 493021-13-9
(2Z,4E)-(R)-6-Acetoxy-7-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-5-oxo-cyclopentyl]-3-ethoxy-hepta-2,4-dienoic acid allyl ester

: 493021-08-2
(4S,5S,8R,9S,10R,11R,13R,14S,17S)-11-Acetoxy-4-(tert-butyl-diphenyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxymethyl)-14-hydroxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 84 percent / AcOH / H₂O / 3 h / 80 °C

2.1: Cs₂CO₃ / CH₂Cl₂ / 0.17 h / 20 °C

2.2: 61 percent / CH₂Cl₂ / 4 h / 20 °C

3.1: 71 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾; morpholine / tetrahydrofuran / 3 h / 20 °C

4.1: 71 percent / potassium bis(tetramethylsilyl)amide / tetrahydrofuran / 1.5 h / Heating

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium bis(tetramethylsilyl)amide; caesium carbonate; acetic acid; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol027125o

Reference yield:

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

: 493021-08-2
(4S,5S,8R,9S,10R,11R,13R,14S,17S)-11-Acetoxy-4-(tert-butyl-diphenyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxymethyl)-14-hydroxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 17 steps

1.1: 94 percent / sodium borohydride / ethanol / 4 h / -15 °C

2.1: 93 percent / pyridine; 4-(dimethylamino)pyridine / 0 - 20 °C

3.1: 85 percent / dimethylsulfoxide / 3 h / 20 °C

4.1: 95 percent / pTSA / benzene / 5 h / Heating

5.1: 91 percent / diisobutylaluminum hydride / toluene / 1 h / 0 °C

6.1: 96 percent / sodium borohydride / ethanol / 1.5 h / -20 °C

7.1: 95 percent / HCl / acetone / 2 h / 20 °C

8.1: 99 percent / imidazole / dimethylformamide / 0 - 20 °C

9.1: toluene / 31 h / 138 °C

10.1: 80 percent / sodium periodate; RuCl₃ / H₂O; CCl₄; acetonitrile / 7 h / 20 °C

11.1: 81 percent / N,N'-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

12.1: triethylsilane; Pd(OAc)2; molecular sieves 4 Angstroem / acetone / 20 °C

13.1: 0.062 mg / benzene / 11 h / Heating

14.1: 84 percent / AcOH / H₂O / 3 h / 80 °C

15.1: Cs₂CO₃ / CH₂Cl₂ / 0.17 h / 20 °C

15.2: 61 percent / CH₂Cl₂ / 4 h / 20 °C

16.1: 71 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾; morpholine / tetrahydrofuran / 3 h / 20 °C

17.1: 71 percent / potassium bis(tetramethylsilyl)amide / tetrahydrofuran / 1.5 h / Heating

With morpholine; pyridine; 1H-imidazole; hydrogenchloride; triethylsilane; dmap; ruthenium trichloride; palladium diacetate; sodium tetrahydroborate; sodium periodate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 4 A molecular sieve; potassium bis(tetramethylsilyl)amide; diisobutylaluminium hydride; caesium carbonate; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene; 13.1: Wittig reaction;
DOI:10.1021/ol027125o