(Z)-(2S,9S,10R)-9-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-2-methyl-undec-6-en-1-ol

Base Information

• Chemical Name: (Z)-(2S,9S,10R)-9-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-2-methyl-undec-6-en-1-ol
• CAS No.: 201936-47-2
• Molecular Formula: C₃₄H₅₆O₃Si₂
• Molecular Weight: 568.988

Synonyms:(Z)-(2S,9S,10R)-9-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-2-methyl-undec-6-en-1-ol

Chemical Property of (Z)-(2S,9S,10R)-9-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-2-methyl-undec-6-en-1-ol

Chemical Property:

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Technology Process of (Z)-(2S,9S,10R)-9-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-2-methyl-undec-6-en-1-ol

There total 10 articles about (Z)-(2S,9S,10R)-9-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-2-methyl-undec-6-en-1-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: 92.0%

(Z)-(2S,9S,10R)-9-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-methyl-undec-6-en-1-one (201936-46-1) → (Z)-(2S,9S,10R)-9-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-2-methyl-undec-6-en-1-ol (201936-47-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(97)10527-5

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (Z)-(2S,9S,10R)-9-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-2-methyl-undec-6-en-1-ol (201936-47-2)

Guidance literature:

Multi-step reaction with 9 steps

1: imidazole, 4-N,N'-dimethylaminopyridine / CH₂Cl₂

2: 1.) n-BuLi, Me₂AlCl / 2.) toluene, 0 deg C to ambient temp.

3: 94 percent / H₂, quinoline / Lindelar's catalyst / ethanol

4: 93 percent / 0.1N HCl / ethanol

5: 89 percent / pyridien, DMAP / CH₂Cl₂

6: 93 percent / 2,6-lutidine / CH₂Cl₂

7: 94 percent / NaI / acetone

8: 68 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 0 °C

9: 92 percent / LiAlH₄ / tetrahydrofuran / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; quinoline; hydrogenchloride; dmap; lithium aluminium tetrahydride; n-butyllithium; hydrogen; dimethylaluminum chloride; sodium iodide; Lindlar's catalyst; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; acetone;

DOI:10.1016/S0040-4039(97)10527-5

Reference yield:

tert-Butyl-((R)-(S)-1-oxiranyl-ethoxy)-diphenyl-silane (201936-38-1) → (Z)-(2S,9S,10R)-9-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-2-methyl-undec-6-en-1-ol (201936-47-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) n-BuLi, Me₂AlCl / 2.) toluene, 0 deg C to ambient temp.

2: 94 percent / H₂, quinoline / Lindelar's catalyst / ethanol

3: 93 percent / 0.1N HCl / ethanol

4: 89 percent / pyridien, DMAP / CH₂Cl₂

5: 93 percent / 2,6-lutidine / CH₂Cl₂

6: 94 percent / NaI / acetone

7: 68 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 0 °C

8: 92 percent / LiAlH₄ / tetrahydrofuran / 0 °C

With pyridine; 2,6-dimethylpyridine; quinoline; hydrogenchloride; dmap; lithium aluminium tetrahydride; n-butyllithium; hydrogen; dimethylaluminum chloride; sodium iodide; Lindlar's catalyst; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; acetone;

DOI:10.1016/S0040-4039(97)10527-5

upstream raw materials:

(Z)-(2S,9S,10R)-9-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methyl-undec-6-en-1-one

t-butyldimethylsiyl triflate

tert-butylchlorodiphenylsilane

tert-Butyl-((R)-(S)-1-oxiranyl-ethoxy)-diphenyl-silane

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