(2S,5S)-5-(2-Benzyloxy-ethyl)-2-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-heptan-3-one

Base Information

Chemical Name:(2S,5S)-5-(2-Benzyloxy-ethyl)-2-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-heptan-3-one
CAS No.:400643-73-4
Molecular Formula:C₅₂H₇₂O₃Si
Molecular Weight:773.227
Hs Code.:

(2S,5S)-5-(2-Benzyloxy-ethyl)-2-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-heptan-3-one

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Chemical Property of (2S,5S)-5-(2-Benzyloxy-ethyl)-2-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-heptan-3-one

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Technology Process of (2S,5S)-5-(2-Benzyloxy-ethyl)-2-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-heptan-3-one

There total 14 articles about (2S,5S)-5-(2-Benzyloxy-ethyl)-2-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-heptan-3-one 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:

: 5989-27-5,555-08-8,8022-90-0,9003-73-0,95327-98-3
D-limonene

: 400643-73-4
(2S,5S)-5-(2-Benzyloxy-ethyl)-2-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-heptan-3-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: H₂ / PtO₂ / methanol

2.1: O₃ / CH₂Cl₂; methanol / 1 h / -60 °C

2.2: p-TsOH / methanol / 1 h / -60 - 0 °C

3.1: 100 percent / HClO₄ / H₂O; tetrahydrofuran

4.1: 98 percent / lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride / tetrahydrofuran / 1 h / -78 °C

5.1: 96 percent / DBU / CH₂Cl₂

6.1: 100 percent / MCPBA / CHCl₃ / 48 h / Heating

7.1: 60 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

8.1: 57 percent / Ag₂O / CH₂Cl₂

9.1: 81 percent / K₂CO₃ / methanol / 8 h / 40 °C

10.1: 66 percent / pyridinium dichromate; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h

11.1: <2.0 equiv. Me₂AlCl / CH₂Cl₂

With dipyridinium dichromate; perchloric acid; Lithium tris[(3-ethyl-3-pentyl)-oxy]aluminohydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; dimethylaluminum chloride; potassium carbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide; platinum(IV) oxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; 6.1: Baeyer-Villiger reaction / 11.1: Oppenhauer-like oxidation;
DOI:10.1016/S0040-4039(01)01964-5

Reference yield:

: 67304-08-9
(R)-3-isopropyl-6-oxoheptanal

: 400643-73-4
(2S,5S)-5-(2-Benzyloxy-ethyl)-2-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-heptan-3-one

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride / tetrahydrofuran / 1 h / -78 °C

2: 96 percent / DBU / CH₂Cl₂

3: 100 percent / MCPBA / CHCl₃ / 48 h / Heating

4: 60 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

5: 57 percent / Ag₂O / CH₂Cl₂

6: 81 percent / K₂CO₃ / methanol / 8 h / 40 °C

7: 66 percent / pyridinium dichromate; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h

8: <2.0 equiv. Me₂AlCl / CH₂Cl₂

With dipyridinium dichromate; Lithium tris[(3-ethyl-3-pentyl)-oxy]aluminohydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; dimethylaluminum chloride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; 3: Baeyer-Villiger reaction / 8: Oppenhauer-like oxidation;
DOI:10.1016/S0040-4039(01)01964-5

Reference yield:

: 481-29-8
Epiandrosterone

: 400643-73-4
(2S,5S)-5-(2-Benzyloxy-ethyl)-2-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-heptan-3-one

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / DBU / CH₂Cl₂

2: 98 percent / t-BuOK / tetrahydrofuran / 3 h / Heating

3: <2.0 equiv. Me₂AlCl / CH₂Cl₂

With potassium tert-butylate; dimethylaluminum chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; 3: Oppenhauer-like oxidation;
DOI:10.1016/S0040-4039(01)01964-5