[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

Base Information

Chemical Name:[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
CAS No.:502761-44-6
Molecular Formula:C₃₆H₄₄O₆Si
Molecular Weight:600.827
Hs Code.:

[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

Synonyms:[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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Chemical Property of [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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Technology Process of [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

There total 20 articles about [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 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: 85.0%

: 502761-43-5
[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

: 502761-44-6
[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

Guidance literature:: With hydrogenchloride; In methanol; Heating;
DOI:10.1021/jo026676p

Reference yield: 83.0%

: 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

: 502761-44-6
[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

Guidance literature:: With hydrogenchloride; methanol; for 1h; Heating;
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

: 502761-44-6
[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

Guidance literature:: Multi-step reaction with 8 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

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