[4S-(4β,5β,9α,10β,13β,17β)]-4-(tert-butyldiphenylsilanyloxy)-17-methoxymethoxy-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)]-4-(tert-butyldiphenylsilanyloxy)-17-methoxymethoxy-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.:502761-45-7
Molecular Formula:C₃₈H₄₈O₇Si
Molecular Weight:644.88
Hs Code.:

[4S-(4β,5β,9α,10β,13β,17β)]-4-(tert-butyldiphenylsilanyloxy)-17-methoxymethoxy-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

Synonyms:[4S-(4β,5β,9α,10β,13β,17β)]-4-(tert-butyldiphenylsilanyloxy)-17-methoxymethoxy-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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Chemical Property of [4S-(4β,5β,9α,10β,13β,17β)]-4-(tert-butyldiphenylsilanyloxy)-17-methoxymethoxy-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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Technology Process of [4S-(4β,5β,9α,10β,13β,17β)]-4-(tert-butyldiphenylsilanyloxy)-17-methoxymethoxy-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 11 articles about [4S-(4β,5β,9α,10β,13β,17β)]-4-(tert-butyldiphenylsilanyloxy)-17-methoxymethoxy-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: 55.0%

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

: 502764-68-3
[1S-(1β,3aβ,7aβ)]-3-[1,3a-bis(methoxymethoxy)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]-3-oxopropionic acid allyl ester

: 502761-45-7
[4S-(4β,5β,9α,10β,13β,17β)]-4-(tert-butyldiphenylsilanyloxy)-17-methoxymethoxy-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

Guidance literature:: (4S)-4-t-butyldiphenylsilyloxy-2-carbomethoxycyclohex-2-en-1-one; [1S-(1β,3aβ,7aβ)]-3-[1,3a-bis(methoxymethoxy)-7a-methyl-2,3,3a,6,7,7a-hexahydro-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:

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

: 502761-45-7
[4S-(4β,5β,9α,10β,13β,17β)]-4-(tert-butyldiphenylsilanyloxy)-17-methoxymethoxy-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

Guidance literature:: Multi-step reaction with 11 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

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

Reference yield:

: 502761-53-7
[1S-(1β,4aβ,5β)]-5-methoxymethoxy-4a-methyl-octahydro-1-oxa-cyclopropa[d]indene

: 502761-45-7
[4S-(4β,5β,9α,10β,13β,17β)]-4-(tert-butyldiphenylsilanyloxy)-17-methoxymethoxy-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

Guidance literature:: Multi-step reaction with 10 steps

1.1: 81 percent / KOH / H₂O; dimethylsulfoxide / 16 h / 120 °C

2.1: 100 percent / triethylamine / tetrahydrofuran / 2 h / 20 °C

3.1: 100 percent / N,N-diisopropylethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 72.17 h / 0 - 20 °C

4.1: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C

5.1: 100 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

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

6.2: 92 percent / tetrahydrofuran / 2 h / -30 °C

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

8.1: 117 mg / oxalic acid; water / dimethylformamide / 2 h / 20 °C

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

9.2: 87 percent / tetrahydrofuran / 0.25 h / -78 °C

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

10.2: 55 percent / morpholine / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 3 h / 20 °C

With dmap; potassium hydroxide; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; oxalic acid; caesium carbonate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium hexamethyldisilazane; bis(triphenylphosphine)palladium(II)-chloride; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 7.1: Stille coupling;
DOI:10.1021/jo026676p