(1S,12S)-14-[(E)-18-(tert-butyldiphenylsilanyloxy)vinyl]-3-methyl-16-(toluene-4-sulfonyl)-3,16-diazatetracyclo[10.3.1.0^2,10.0^4,9]hexadeca-2⁽¹⁰⁾,4,6,8,13-pentane

Base Information

• Chemical Name: (1S,12S)-14-[(E)-18-(tert-butyldiphenylsilanyloxy)vinyl]-3-methyl-16-(toluene-4-sulfonyl)-3,16-diazatetracyclo[10.3.1.0^2,10.0^4,9]hexadeca-2⁽¹⁰⁾,4,6,8,13-pentane
• CAS No.: 860438-76-2
• Molecular Formula: C₄₀H₄₂N₂O₃SSi
• Molecular Weight: 658.937

Synonyms:(1S,12S)-14-[(E)-18-(tert-butyldiphenylsilanyloxy)vinyl]-3-methyl-16-(toluene-4-sulfonyl)-3,16-diazatetracyclo[10.3.1.0^2,10.0^4,9]hexadeca-2⁽¹⁰⁾,4,6,8,13-pentane

Chemical Property of (1S,12S)-14-[(E)-18-(tert-butyldiphenylsilanyloxy)vinyl]-3-methyl-16-(toluene-4-sulfonyl)-3,16-diazatetracyclo[10.3.1.0^2,10.0^4,9]hexadeca-2⁽¹⁰⁾,4,6,8,13-pentane

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Technology Process of (1S,12S)-14-[(E)-18-(tert-butyldiphenylsilanyloxy)vinyl]-3-methyl-16-(toluene-4-sulfonyl)-3,16-diazatetracyclo[10.3.1.0^2,10.0^4,9]hexadeca-2⁽¹⁰⁾,4,6,8,13-pentane

There total 8 articles about (1S,12S)-14-[(E)-18-(tert-butyldiphenylsilanyloxy)vinyl]-3-methyl-16-(toluene-4-sulfonyl)-3,16-diazatetracyclo[10.3.1.0^2,10.0^4,9]hexadeca-2⁽¹⁰⁾,4,6,8,13-pentane 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: 95.0%

(1S,12S)-3-methyl-14-[[phenylsulfonyl]-18-oxoethyl]-16-(toluene-4-sulfonyl)-3,16-diazatetracyclo[10.3.1.02,10.04,9]hexadeca-2(10),4,6,8-tetraene (860438-75-1) + tert-butylchlorodiphenylsilane (58479-61-1) → (1S,12S)-14-[(E)-18-(tert-butyldiphenylsilanyloxy)vinyl]-3-methyl-16-(toluene-4-sulfonyl)-3,16-diazatetracyclo[10.3.1.02,10.04,9]hexadeca-2(10),4,6,8,13-pentane (860438-76-2)

Guidance literature:

With dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2005.04.033

Reference yield:

1-methyl-3-[(2S)-1-(toluene-4-sulfonyl)aziridin-2-ylmethyl]-1H-indole (860438-73-9) → (1S,12S)-14-[(E)-18-(tert-butyldiphenylsilanyloxy)vinyl]-3-methyl-16-(toluene-4-sulfonyl)-3,16-diazatetracyclo[10.3.1.02,10.04,9]hexadeca-2(10),4,6,8,13-pentane (860438-76-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 72 percent / lithium naphthalenide; DMPU / tetrahydrofuran / -78 - 20 °C

2.1: 61 percent / KMnO₄; nBu₄NBr / CH₂Cl₂ / 3 - 20 °C

3.1: Pb(OAc)4; NaHCO₃ / 1,2-dichloro-ethane / 0.5 h / 0 °C

3.2: 94 percent / MgSO₄; TEA / CH₂Cl₂ / 0.83 h / 20 °C

4.1: 95 percent / DMAP; DBU / CH₂Cl₂ / 1.5 h / 0 °C

With lead(IV) acetate; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium permanganate; tetrabutylammomium bromide; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; naphthalen-1-yl-lithium; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; 3.2: Pictet-Spengler-type bicyclization;

DOI:10.1016/j.tetlet.2005.04.033

Reference yield:

(2S)-3-(1-methyl-1H-indol-3-yl)-2-[(toluene-4-sulfonyl)amino]propanol → (1S,12S)-14-[(E)-18-(tert-butyldiphenylsilanyloxy)vinyl]-3-methyl-16-(toluene-4-sulfonyl)-3,16-diazatetracyclo[10.3.1.02,10.04,9]hexadeca-2(10),4,6,8,13-pentane (860438-76-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 80 percent / KOH; tosyl chloride / diethyl ether; tetrahydrofuran

2.1: 72 percent / lithium naphthalenide; DMPU / tetrahydrofuran / -78 - 20 °C

3.1: 61 percent / KMnO₄; nBu₄NBr / CH₂Cl₂ / 3 - 20 °C

4.1: Pb(OAc)4; NaHCO₃ / 1,2-dichloro-ethane / 0.5 h / 0 °C

4.2: 94 percent / MgSO₄; TEA / CH₂Cl₂ / 0.83 h / 20 °C

5.1: 95 percent / DMAP; DBU / CH₂Cl₂ / 1.5 h / 0 °C

With lead(IV) acetate; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hydroxide; potassium permanganate; tetrabutylammomium bromide; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; naphthalen-1-yl-lithium; p-toluenesulfonyl chloride; In tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane; 4.2: Pictet-Spengler-type bicyclization;

DOI:10.1016/j.tetlet.2005.04.033

upstream raw materials:

(1S,12S)-3-methyl-14-[[phenylsulfonyl]-18-oxoethyl]-16-(toluene-4-sulfonyl)-3,16-diazatetracyclo[10.3.1.0^2,10.0^4,9]hexadeca-2⁽¹⁰⁾,4,6,8-tetraene

tert-butylchlorodiphenylsilane

1-methyl-3-[(2S)-1-(toluene-4-sulfonyl)aziridin-2-ylmethyl]-1H-indole

N-[(1S)-1-(1-benzenesulfonylcyclopent-3-enylmethyl)-2-(1-methyl-1H-indol-3-yl)ethyl]-4-methylbenzenesulfonamide

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