(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

Base Information

• Chemical Name: (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
• CAS No.: 201936-46-1
• Molecular Formula: C₄₄H₆₉NO₅SSi₂
• Molecular Weight: 780.273

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 9 articles about (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 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: 68.0%

N-propionyl-(2R)-bornane-(10,2)-sultam (125664-95-1) + C31H49IO2Si2 (201936-45-0) → (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)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 - 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)-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)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; quinoline; hydrogenchloride; dmap; 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)-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)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; 2,6-dimethylpyridine; quinoline; hydrogenchloride; dmap; 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:

N-propionyl-(2R)-bornane-(10,2)-sultam

C₃₁H₄₉IO₂Si₂

t-butyldimethylsiyl triflate

tert-butylchlorodiphenylsilane

Downstream raw materials:

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

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