(4E,7S)-N-{(2R)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl]-2-hydroxyethyl}-7-methoxydodec-4-enamide

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Chemical Name:(4E,7S)-N-{(2R)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl]-2-hydroxyethyl}-7-methoxydodec-4-enamide
CAS No.:1309930-59-3
Molecular Formula:C₃₅H₅₉NO₅Si
Molecular Weight:601.943
Hs Code.:
Mol file:1309930-59-3.mol

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

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Chemical Property of (4E,7S)-N-{(2R)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl]-2-hydroxyethyl}-7-methoxydodec-4-enamide Edit

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

There total 13 articles about (4E,7S)-N-{(2R)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl]-2-hydroxyethyl}-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: 85.0%

: 1309930-56-0
(4E,7S)-N-{2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl]-2-oxoethyl}-7-methoxydodec-4-enamide

: 1309930-59-3
(4E,7S)-N-{(2R)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl]-2-hydroxyethyl}-7-methoxydodec-4-enamide

Guidance literature:: With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; at 0 - 20 ℃; for 5.5h; optical yield given as %de; stereoselective reaction;
DOI:10.1039/c0ob01118e

Reference yield:

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

: 1309930-59-3
(4E,7S)-N-{(2R)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl]-2-hydroxyethyl}-7-methoxydodec-4-enamide

Guidance literature:: Multi-step reaction with 8 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

With 4-methyl-morpholine; chromium dichloride; dmap; sodium tetrahydroborate; cerium(III) chloride heptahydrate; dimethylsulfide borane complex; iodine; sodium hydride; benzotriazol-1-ol; Dess-Martin periodane; hydrazine hydrate; dicyclohexyl-carbodiimide; nickel dichloride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; ethanol; dichloromethane; 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:

: 1309930-42-4
(5R,6R)-5-tert-butyldimethylsilyloxy-2-iodo-6-methyl-2-cyclohexenone

: 1309930-59-3
(4E,7S)-N-{(2R)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl]-2-hydroxyethyl}-7-methoxydodec-4-enamide

Guidance literature:: Multi-step reaction with 7 steps

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

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

2.2: 12 h / 20 °C / Inert atmosphere

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

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

5.1: 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane / 8.5 h / 0 - 20 °C

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

7.1: 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

With 4-methyl-morpholine; chromium dichloride; sodium tetrahydroborate; cerium(III) chloride heptahydrate; dimethylsulfide borane complex; sodium hydride; benzotriazol-1-ol; Dess-Martin periodane; hydrazine hydrate; dicyclohexyl-carbodiimide; nickel dichloride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Luche reduction / 3.1: Nozaki-Hiyama-Kishi reaction / 7.1: Corey-Bakshi-Shibata reduction;
DOI:10.1039/c0ob01118e