1-((S)-2-{(R)-2-[(1R,2R,4aS,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-hydroxy-ethyl}-oxiranyl)-ethanone

Base Information

• Chemical Name: 1-((S)-2-{(R)-2-[(1R,2R,4aS,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-hydroxy-ethyl}-oxiranyl)-ethanone
• CAS No.: 263387-45-7
• Molecular Formula: C₃₆H₅₀O₄Si
• Molecular Weight: 574.876
• Mol file: 263387-45-7.mol

Synonyms:

Chemical Property of 1-((S)-2-{(R)-2-[(1R,2R,4aS,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-hydroxy-ethyl}-oxiranyl)-ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-((S)-2-{(R)-2-[(1R,2R,4aS,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-hydroxy-ethyl}-oxiranyl)-ethanone

There total 12 articles about 1-((S)-2-{(R)-2-[(1R,2R,4aS,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-hydroxy-ethyl}-oxiranyl)-ethanone 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: 83.0%

(R)-5-[(1R,2R,4aS,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-4-hydroxy-3-methylene-pentan-2-one (263387-44-6) → 1-((S)-2-{(R)-2-[(1R,2R,4aS,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-hydroxy-ethyl}-oxiranyl)-ethanone (263387-45-7)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; 4 Angstroem MS;

DOI:10.1016/S0040-4039(99)02206-6

Reference yield:

(4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal (26742-33-6) → 1-((S)-2-{(R)-2-[(1R,2R,4aS,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-hydroxy-ethyl}-oxiranyl)-ethanone (263387-45-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 80 percent / Li / liquid ammonia

2.1: 75 percent / t-BuOK

3.1: 80 percent / H₂ / Rh/C

4.1: 100 percent / HCl / tetrahydrofuran; H₂O

5.1: 84 percent / LDA

6.1: 84 percent / Pd(OAc)2; Bu₃SnH

7.1: 96 percent / imidazole

8.1: LAH / diethyl ether / 0 °C

9.1: PCC / CH₂Cl₂

10.1: PhSeTMS; TMSOTf

10.2: 20 percent / NaIO₄

11.1: 83 percent / tBuOOH; Ti(OiPr)4; 4 Angstroem MS

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; palladium diacetate; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; phenyl trimethylsilyl selenide; 4 Angstroem MS; potassium tert-butylate; hydrogen; tri-n-butyl-tin hydride; lithium; pyridinium chlorochromate; lithium diisopropyl amide; Rh on carbon; In tetrahydrofuran; diethyl ether; dichloromethane; ammonia; water; 1.1: Reduction / 1.2: Alkylation / 2.1: Substitution / 3.1: Hydrogenation / 4.1: Hydrolysis / 5.1: Acylation / 6.1: Carbonylation / 7.1: Substitution / 8.1: Reduction / 9.1: Oxidation / 10.1: Addition / 10.2: Oxidation / 11.1: Epoxidation;

DOI:10.1016/S0040-4039(99)02206-6

Reference yield:

C18H28O5 (218453-54-4) → 1-((S)-2-{(R)-2-[(1R,2R,4aS,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-hydroxy-ethyl}-oxiranyl)-ethanone (263387-45-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 75 percent / t-BuOK

2.1: 80 percent / H₂ / Rh/C

3.1: 100 percent / HCl / tetrahydrofuran; H₂O

4.1: 84 percent / LDA

5.1: 84 percent / Pd(OAc)2; Bu₃SnH

6.1: 96 percent / imidazole

7.1: LAH / diethyl ether / 0 °C

8.1: PCC / CH₂Cl₂

9.1: PhSeTMS; TMSOTf

9.2: 20 percent / NaIO₄

10.1: 83 percent / tBuOOH; Ti(OiPr)4; 4 Angstroem MS

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; palladium diacetate; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; phenyl trimethylsilyl selenide; 4 Angstroem MS; potassium tert-butylate; hydrogen; tri-n-butyl-tin hydride; pyridinium chlorochromate; lithium diisopropyl amide; Rh on carbon; In tetrahydrofuran; diethyl ether; dichloromethane; water; 1.1: Substitution / 2.1: Hydrogenation / 3.1: Hydrolysis / 4.1: Acylation / 5.1: Carbonylation / 6.1: Substitution / 7.1: Reduction / 8.1: Oxidation / 9.1: Addition / 9.2: Oxidation / 10.1: Epoxidation;

DOI:10.1016/S0040-4039(99)02206-6

upstream raw materials:

(R)-5-[(1R,2R,4aS,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-4-hydroxy-3-methylene-pentan-2-one

(4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal

tert-butylchlorodiphenylsilane

C₁₈H₂₈O₅