[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

Base Information

Chemical Name:[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
CAS No.:502761-47-9
Molecular Formula:C₄₃H₄₉NO₈Si
Molecular Weight:735.949
Hs Code.:

[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

Synonyms:[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

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Chemical Property of [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

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Technology Process of [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

There total 22 articles about [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 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: 94.0%

: 122-04-3
4-nitro-benzoyl chloride

: 502761-46-8
[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

: 502761-47-9
[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

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1021/jo026676p

Reference yield:

: 140659-36-5
<1S-(1α,7aα)>-1,2,5,6,7,7a-Hexahydro-1-<(tert-butyldimethylsilyl)oxy>-7a-methyl-4H-inden-4-one

: 502761-47-9
[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

Guidance literature:: Multi-step reaction with 10 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

8.1: 85 percent / aq. HCl / methanol / Heating

9.1: 76 percent / hydrogen / palladium on activated carbon / ethanol / 18 h / 20 °C / 760 Torr

10.1: 94 percent / pyridine; 4-dimethylaminopyridine / CH₂Cl₂ / 4 h / 20 °C

With pyridine; hydrogenchloride; dmap; n-butyllithium; hydrogen; diisobutylaluminium hydride; potassium carbonate; caesium carbonate; Dess-Martin periodane; diisopropylamine; palladium on activated charcoal; bis(triphenylphosphine)palladium(II)-chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 4.1: Dess-Martin oxidation / 6.1: Dess-Martin oxidation;
DOI:10.1021/jo026676p

Reference yield:

: 415928-30-2
(3S,3aS)-3-Methoxymethoxy-3a-methyl-2,3,3a,4,5,6-hexahydro-1H-indene

: 502761-47-9
[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

Guidance literature:: Multi-step reaction with 14 steps

1.1: 71 percent / dimethyldioxirane / acetone; CH₂Cl₂ / 1 h / -78 °C

2.1: 81 percent / KOH / H₂O; dimethylsulfoxide / 16 h / 120 °C

3.1: 100 percent / triethylamine / tetrahydrofuran / 2 h / 20 °C

4.1: 100 percent / N,N-diisopropylethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 72.17 h / 0 - 20 °C

5.1: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C

6.1: 100 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

7.1: LiHMDS / tetrahydrofuran / 2 h / -78 °C

7.2: 92 percent / tetrahydrofuran / 2 h / -30 °C

8.1: LiCl / bis(triphenylphosphine)palladium(II) chloride / dimethylformamide / 18 h / 60 °C

9.1: 117 mg / oxalic acid; water / dimethylformamide / 2 h / 20 °C

10.1: LiHMDS / tetrahydrofuran / 2 h / -78 °C

10.2: 87 percent / tetrahydrofuran / 0.25 h / -78 °C

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

11.2: 55 percent / morpholine / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 3 h / 20 °C

12.1: 83 percent / hydrochloric acid; MeOH / 1 h / Heating

13.1: 76 percent / hydrogen / palladium on activated carbon / ethanol / 18 h / 20 °C / 760 Torr

14.1: 94 percent / pyridine; 4-dimethylaminopyridine / CH₂Cl₂ / 4 h / 20 °C

With pyridine; hydrogenchloride; methanol; dmap; potassium hydroxide; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; 3,3-dimethyldioxirane; oxalic acid; caesium carbonate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium hexamethyldisilazane; palladium on activated charcoal; bis(triphenylphosphine)palladium(II)-chloride; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 8.1: Stille coupling;
DOI:10.1021/jo026676p