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

Base Information

Chemical Name:(4E,7S)-N-{(2S)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl]-2-hydroxyethyl}-7-methoxydodec-4-enamide
CAS No.:1309930-51-5
Molecular Formula:C₃₅H₅₉NO₅Si
Molecular Weight:601.943
Hs Code.:

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

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

There total 10 articles about (4E,7S)-N-{(2S)-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:

: C₂₂H₃₇NO₃Si

: 290354-60-8
(4E,7S)-(-)-7-methoxydodec-4-enoic acid

: 1309930-51-5
(4E,7S)-N-{(2S)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl]-2-hydroxyethyl}-7-methoxydodec-4-enamide

Guidance literature:: With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 8.5h;
DOI:10.1039/c0ob01118e

Reference yield:

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

: 1309930-51-5
(4E,7S)-N-{(2S)-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 5 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

With 4-methyl-morpholine; chromium dichloride; sodium tetrahydroborate; cerium(III) chloride heptahydrate; sodium hydride; benzotriazol-1-ol; hydrazine hydrate; dicyclohexyl-carbodiimide; nickel dichloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Luche reduction / 3.1: Nozaki-Hiyama-Kishi reaction;
DOI:10.1039/c0ob01118e

Reference yield:

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

: 1309930-51-5
(4E,7S)-N-{(2S)-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 6 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

With 4-methyl-morpholine; chromium dichloride; dmap; sodium tetrahydroborate; cerium(III) chloride heptahydrate; iodine; sodium hydride; benzotriazol-1-ol; hydrazine hydrate; dicyclohexyl-carbodiimide; nickel dichloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 2.1: Luche reduction / 4.1: Nozaki-Hiyama-Kishi reaction;
DOI:10.1039/c0ob01118e