Technology Process of Acetic acid (R)-2-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-5-oxo-cyclopentyl]-1-((3aS,5S,5aR,6S,9aS,9bR)-5-hydroxy-5a-hydroxymethyl-2,2-dimethyl-8-oxo-decahydro-naphtho[1,2-d][1,3]dioxol-6-yl)-ethyl ester
There total 15 articles about Acetic acid (R)-2-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-5-oxo-cyclopentyl]-1-((3aS,5S,5aR,6S,9aS,9bR)-5-hydroxy-5a-hydroxymethyl-2,2-dimethyl-8-oxo-decahydro-naphtho[1,2-d][1,3]dioxol-6-yl)-ethyl 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:
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![acetic acid 17-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-4,14-dihydroxy-13-methyl-1,7-dioxo-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1<i>H</i>-cyclopenta[<i>a</i>]phenanthren-11-yl ester](/Databaselist/images/loading.webp)
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872525-89-8
acetic acid 17-(tert-butyl-diphenyl-silanyloxymethyl)-4,14-dihydroxy-13-methyl-1,7-dioxo-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-11-yl ester
- Guidance literature:
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With
Ne4NHB(OAc)3; acetic acid;
In
acetonitrile;
at -20 - 0 ℃;
for 19h;
DOI:10.1139/v05-042
- Guidance literature:
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Multi-step reaction with 6 steps
1: 77 percent / cesium carbonate / CH2Cl2 / 2 h / 20 °C
2: 86 percent / morpholine / tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 0.08 h / 20 °C
3: 99 percent / LiAlH[OC(C2H5)3]3 / tetrahydrofuran / 1 h / 0 °C
4: 71 percent / diisopropylethylamine / CH2Cl2 / 16 h / 20 °C
5: 28 percent / potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h / Heating
6: 96 percent / Ne4NHB(OAc)3; acetic acid / acetonitrile / 19 h / -20 - 0 °C
With
morpholine; lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride; Ne4NHB(OAc)3; potassium hexamethylsilazane; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; dichloromethane; toluene; acetonitrile;
5: aldol condensation;
DOI:10.1139/v05-042
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 3.00 g / tetrahydrofuran; toluene / 1 h / 0 °C
2.1: 92 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 1 h / -78 °C
3.1: t-butyllithium / diethyl ether; pentane / 4 h / 0 °C
3.2: 98 percent / diethyl ether; pentane / 0.5 h / 0 °C
4.1: 73 percent / Grubb's second generation catalyst / CH2Cl2 / 40 °C
5.1: 80 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
6.1: 77 percent / cesium carbonate / CH2Cl2 / 2 h / 20 °C
7.1: 86 percent / morpholine / tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 0.08 h / 20 °C
8.1: 99 percent / LiAlH[OC(C2H5)3]3 / tetrahydrofuran / 1 h / 0 °C
9.1: 71 percent / diisopropylethylamine / CH2Cl2 / 16 h / 20 °C
10.1: 28 percent / potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h / Heating
11.1: 96 percent / Ne4NHB(OAc)3; acetic acid / acetonitrile / 19 h / -20 - 0 °C
With
morpholine; lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride; Ne4NHB(OAc)3; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; caesium carbonate; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile; pentane;
1.1: Wittig reaction / 10.1: aldol condensation;
DOI:10.1139/v05-042
