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

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Chemical Name:(4E,7S)-N-{(2R)-2-[(4R,5R)-4-hydroxy-5-methyl-6-oxocyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide
CAS No.:485388-83-8
Molecular Formula:C₂₃H₃₉NO₅
Molecular Weight:409.566
Hs Code.:

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

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

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

There total 17 articles about (4E,7S)-N-{(2R)-2-[(4R,5R)-4-hydroxy-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: 69.0%

: 1309930-62-8
(4E,7S)-N-{(2R)-2-[(4R,5R)-4-(tert-butyldimethylsilyloxy)-5-methyl-6-oxocyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide

: 485388-83-8
(4E,7S)-N-{(2R)-2-[(4R,5R)-4-hydroxy-5-methyl-6-oxocyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide

Guidance literature:: With water; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 20h;
DOI:10.1039/c0ob01118e

Reference yield:

: 1309930-37-7
(5R,6R)-5-tert-butyldimethylsilyloxy-6-methyl-2-cyclohexenone

: 485388-83-8
(4E,7S)-N-{(2R)-2-[(4R,5R)-4-hydroxy-5-methyl-6-oxocyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide

Guidance literature:: Multi-step reaction with 12 steps

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

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

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

3.2: 12 h / 20 °C / Inert atmosphere

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

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

6.1: 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane / 8.5 h / 0 - 20 °C

7.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

8.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 5.5 h / 0 - 20 °C

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

10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 12 h

11.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

12.1: water; trifluoroacetic acid / dichloromethane / 20 h / 0 °C

With 4-methyl-morpholine; chromium dichloride; dmap; calcium sulfate; sodium tetrahydroborate; cerium(III) chloride heptahydrate; dimethylsulfide borane complex; water; iodine; sodium hydride; benzotriazol-1-ol; Dess-Martin periodane; hydrazine hydrate; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; silver(l) oxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 2.1: Luche reduction / 4.1: Nozaki-Hiyama-Kishi reaction / 8.1: Corey-Bakshi-Shibata reduction;
DOI:10.1039/c0ob01118e

Reference yield:

: 1309930-44-6
(1R,5R,6S)-5-tert-butyldimethylsilyloxy-2-iodo-6-methylcyclohex-2-enol

: 485388-83-8
(4E,7S)-N-{(2R)-2-[(4R,5R)-4-hydroxy-5-methyl-6-oxocyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide

Guidance literature:: Multi-step reaction with 10 steps

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

1.2: 12 h / 20 °C / Inert atmosphere

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

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

4.1: 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane / 8.5 h / 0 - 20 °C

5.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

6.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 5.5 h / 0 - 20 °C

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

8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 12 h

9.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

10.1: water; trifluoroacetic acid / dichloromethane / 20 h / 0 °C

With 4-methyl-morpholine; chromium dichloride; calcium sulfate; dimethylsulfide borane complex; water; sodium hydride; benzotriazol-1-ol; Dess-Martin periodane; hydrazine hydrate; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; silver(l) oxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 2.1: Nozaki-Hiyama-Kishi reaction / 6.1: Corey-Bakshi-Shibata reduction;
DOI:10.1039/c0ob01118e