(4E,7S)-N-{(2S)-2-[(4R,5R)-4-(tert-butyldimethylsilyloxy)-5-methyl-6-oxocyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide

Base Information

• Chemical Name: (4E,7S)-N-{(2S)-2-[(4R,5R)-4-(tert-butyldimethylsilyloxy)-5-methyl-6-oxocyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide
• CAS No.: 1309930-55-9
• Molecular Formula: C₂₉H₅₃NO₅Si
• Molecular Weight: 523.829
• Mol file: 1309930-55-9.mol

Synonyms:(4E,7S)-N-{(2S)-2-[(4R,5R)-4-(tert-butyldimethylsilyloxy)-5-methyl-6-oxocyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide

Chemical Property of (4E,7S)-N-{(2S)-2-[(4R,5R)-4-(tert-butyldimethylsilyloxy)-5-methyl-6-oxocyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4E,7S)-N-{(2S)-2-[(4R,5R)-4-(tert-butyldimethylsilyloxy)-5-methyl-6-oxocyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide

There total 15 articles about (4E,7S)-N-{(2S)-2-[(4R,5R)-4-(tert-butyldimethylsilyloxy)-5-methyl-6-oxocyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide 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: 75.0%

(4E,7S)-N-{(2S)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methyl-cyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide (1309930-54-8) → (4E,7S)-N-{(2S)-2-[(4R,5R)-4-(tert-butyldimethylsilyloxy)-5-methyl-6-oxocyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide (1309930-55-9)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; for 12h;

DOI:10.1039/c0ob01118e

Reference yield:

[(1R,5R,6S)-5-benzyloxy-4-iodo-6-methylcyclohex-3-enyloxy]-tert-butyldimethylsilane (1309930-46-8) → (4E,7S)-N-{(2S)-2-[(4R,5R)-4-(tert-butyldimethylsilyloxy)-5-methyl-6-oxocyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide (1309930-55-9)

Guidance literature:

Multi-step reaction with 5 steps

1: chromium dichloride; nickel dichloride / N,N-dimethyl-formamide / 36 h / 28 °C

2: hydrazine hydrate / ethanol / 2 h / 60 °C

3: 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane / 8.5 h / 0 - 20 °C

4: calcium sulfate; silver(l) oxide / 24 h / 40 °C

5: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 12 h

With 4-methyl-morpholine; chromium dichloride; calcium sulfate; benzotriazol-1-ol; hydrazine hydrate; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; silver(l) oxide; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Nozaki-Hiyama-Kishi reaction;

DOI:10.1039/c0ob01118e

Reference yield:

(R)-Carvone (6485-40-1,2244-16-8) → (4E,7S)-N-{(2S)-2-[(4R,5R)-4-(tert-butyldimethylsilyloxy)-5-methyl-6-oxocyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide (1309930-55-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: dihydrogen peroxide; sodium hydroxide / methanol; water / -20 °C

2.1: N-acetylcystein; diphenyl diselenide; sodium hydroxide / methanol / 1.5 h / Inert atmosphere

3.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 0 - 20 °C

4.1: ozone / methanol; dichloromethane / -78 °C

4.2: 0.33 h / -20 °C

4.3: 10 h / -20 - 20 °C

5.1: dmap; iodine / dichloromethane / 10.3 h / 20 °C

6.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol; dichloromethane / 0.5 h / 0 °C

7.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

7.2: 12 h / 20 °C / Inert atmosphere

8.1: chromium dichloride; nickel dichloride / N,N-dimethyl-formamide / 36 h / 28 °C

9.1: hydrazine hydrate / ethanol / 2 h / 60 °C

10.1: 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane / 8.5 h / 0 - 20 °C

11.1: calcium sulfate; silver(l) oxide / 24 h / 40 °C

12.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 12 h

With 4-methyl-morpholine; 1H-imidazole; chromium dichloride; dmap; calcium sulfate; sodium tetrahydroborate; N-acetylcystein; cerium(III) chloride heptahydrate; diphenyl diselenide; dihydrogen peroxide; iodine; sodium hydride; benzotriazol-1-ol; ozone; hydrazine hydrate; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; nickel dichloride; silver(l) oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 6.1: Luche reduction / 8.1: Nozaki-Hiyama-Kishi reaction;

DOI:10.1039/c0ob01118e

upstream raw materials:

(5R,6R)-5-tert-butyldimethylsilyloxy-6-methyl-2-cyclohexenone

(5R,6R)-5-tert-butyldimethylsilyloxy-2-iodo-6-methyl-2-cyclohexenone

(1R,5R,6S)-5-tert-butyldimethylsilyloxy-2-iodo-6-methylcyclohex-2-enol

[(1R,5R,6S)-5-benzyloxy-4-iodo-6-methylcyclohex-3-enyloxy]-tert-butyldimethylsilane

Downstream raw materials:

(4E,7S)-N-{(2S)-2-[(4R,5R)-4-hydroxy-5-methyl-6-oxocyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide

Refernces