(4S,6R)-6-{(S)-1-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethyl}-4-isopropyl-tetrahydro-pyran-2-ol

Base Information

• Chemical Name: (4S,6R)-6-{(S)-1-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethyl}-4-isopropyl-tetrahydro-pyran-2-ol
• CAS No.: 400643-58-5
• Molecular Formula: C₄₅H₆₈O₃Si
• Molecular Weight: 685.119
• Mol file: 400643-58-5.mol

Synonyms:(4S,6R)-6-{(S)-1-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethyl}-4-isopropyl-tetrahydro-pyran-2-ol

Chemical Property of (4S,6R)-6-{(S)-1-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethyl}-4-isopropyl-tetrahydro-pyran-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,6R)-6-{(S)-1-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethyl}-4-isopropyl-tetrahydro-pyran-2-ol

There total 16 articles about (4S,6R)-6-{(S)-1-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethyl}-4-isopropyl-tetrahydro-pyran-2-ol 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: 98.0%

(4S,6R)-6-{(S)-1-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethyl}-4-isopropyl-tetrahydro-pyran-2-one (400643-83-6) → (4S,6R)-6-{(S)-1-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethyl}-4-isopropyl-tetrahydro-pyran-2-ol (400643-58-5)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4039(01)01964-5

Reference yield:

(R)-3-isopropyl-6-oxoheptanal (67304-08-9) → (4S,6R)-6-{(S)-1-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethyl}-4-isopropyl-tetrahydro-pyran-2-ol (400643-58-5)

Guidance literature:

Multi-step reaction with 11 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: 66 percent / pyridinium dichromate; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h

6: <2.0 equiv. Me₂AlCl / CH₂Cl₂

7: 56 percent / NaBH₄ / ethanol; tetrahydrofuran

8: 100 percent / K₂CO₃ / methanol

9: 100 percent / H₂ / Pt/C / ethanol

10: 70 percent / RuCl₂(PPh₃)3 / benzene / 6 h

11: 98 percent / DIBAL-H / CH₂Cl₂ / -78 °C

With sodium tetrahydroborate; dipyridinium dichromate; tris(triphenylphosphine)ruthenium(II) chloride; Lithium tris[(3-ethyl-3-pentyl)-oxy]aluminohydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; dimethylaluminum chloride; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; platinum on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; benzene; 3: Baeyer-Villiger reaction / 6: Oppenhauer-like oxidation;

DOI:10.1016/S0040-4039(01)01964-5

Reference yield:

(+)-p-menth-1-ene (1195-31-9,5502-88-5,34363-01-4) → (4S,6R)-6-{(S)-1-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethyl}-4-isopropyl-tetrahydro-pyran-2-ol (400643-58-5)

Guidance literature:

Multi-step reaction with 13 steps

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

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

2.1: 100 percent / HClO₄ / H₂O; tetrahydrofuran

3.1: 98 percent / lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride / tetrahydrofuran / 1 h / -78 °C

4.1: 96 percent / DBU / CH₂Cl₂

5.1: 100 percent / MCPBA / CHCl₃ / 48 h / Heating

6.1: 60 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

7.1: 66 percent / pyridinium dichromate; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h

8.1: <2.0 equiv. Me₂AlCl / CH₂Cl₂

9.1: 56 percent / NaBH₄ / ethanol; tetrahydrofuran

10.1: 100 percent / K₂CO₃ / methanol

11.1: 100 percent / H₂ / Pt/C / ethanol

12.1: 70 percent / RuCl₂(PPh₃)3 / benzene / 6 h

13.1: 98 percent / DIBAL-H / CH₂Cl₂ / -78 °C

With sodium tetrahydroborate; dipyridinium dichromate; tris(triphenylphosphine)ruthenium(II) chloride; perchloric acid; Lithium tris[(3-ethyl-3-pentyl)-oxy]aluminohydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; dimethylaluminum chloride; diisobutylaluminium hydride; potassium carbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; platinum on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; benzene; 5.1: Baeyer-Villiger reaction / 8.1: Oppenhauer-like oxidation;

DOI:10.1016/S0040-4039(01)01964-5

upstream raw materials:

(4S,6R)-6-{(S)-1-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethyl}-4-isopropyl-tetrahydro-pyran-2-one

(R)-3-isopropyl-6-oxoheptanal

D-limonene

(+)-p-menth-1-ene