(2E,4R,6E,8E,10S,11R,12S,14R)-ethyl 15-(3-amino-5-methoxyphenyl)-11,12-dimethoxy-2,4,8,10,14-pentamethylpentadeca-2,6,8-trienoate

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Chemical Name:(2E,4R,6E,8E,10S,11R,12S,14R)-ethyl 15-(3-amino-5-methoxyphenyl)-11,12-dimethoxy-2,4,8,10,14-pentamethylpentadeca-2,6,8-trienoate
CAS No.:1332626-38-6
Molecular Formula:C₃₁H₄₉NO₅
Molecular Weight:515.734
Hs Code.:

Synonyms:(2E,4R,6E,8E,10S,11R,12S,14R)-ethyl 15-(3-amino-5-methoxyphenyl)-11,12-dimethoxy-2,4,8,10,14-pentamethylpentadeca-2,6,8-trienoate

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Chemical Property of (2E,4R,6E,8E,10S,11R,12S,14R)-ethyl 15-(3-amino-5-methoxyphenyl)-11,12-dimethoxy-2,4,8,10,14-pentamethylpentadeca-2,6,8-trienoate

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Technology Process of (2E,4R,6E,8E,10S,11R,12S,14R)-ethyl 15-(3-amino-5-methoxyphenyl)-11,12-dimethoxy-2,4,8,10,14-pentamethylpentadeca-2,6,8-trienoate

There total 10 articles about (2E,4R,6E,8E,10S,11R,12S,14R)-ethyl 15-(3-amino-5-methoxyphenyl)-11,12-dimethoxy-2,4,8,10,14-pentamethylpentadeca-2,6,8-trienoate 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:

: 1332626-16-0
(R,E)-ethyl 2,4-dimethylhept-2-en-6-ynoate

: 1332626-22-8
3-((2R,4S,5R,6S)-4,5-dimethoxy-2,6-dimethylnon-7-yn-1-yl)-5-methoxyaniline

: (2E,4R,10S,11R,12S,14R)-ethyl 15-(3-amino-5-methoxyphenyl)-11,12-dimethoxy-2,4,8,10,14-pentamethylpentadeca-2,6,8-trienoate

: 1332626-38-6
(2E,4R,6E,8E,10S,11R,12S,14R)-ethyl 15-(3-amino-5-methoxyphenyl)-11,12-dimethoxy-2,4,8,10,14-pentamethylpentadeca-2,6,8-trienoate

Guidance literature:: 3-((2R,4S,5R,6S)-4,5-dimethoxy-2,6-dimethylnon-7-yn-1-yl)-5-methoxyaniline; With titanium(IV) isopropylate; cyclopentylmagnesium chloride; In diethyl ether; at -78 - -30 ℃; for 1.5h; Inert atmosphere;

(R,E)-ethyl 2,4-dimethylhept-2-en-6-ynoate; In diethyl ether; at -78 - -30 ℃; for 2h; optical yield given as %de; Inert atmosphere;
DOI:10.1021/ol2019828

Reference yield:

: 1332626-17-1
N,N-diallyl-3-bromo-5-methoxyaniline

: (2E,4R,10S,11R,12S,14R)-ethyl 15-(3-amino-5-methoxyphenyl)-11,12-dimethoxy-2,4,8,10,14-pentamethylpentadeca-2,6,8-trienoate

: 1332626-38-6
(2E,4R,6E,8E,10S,11R,12S,14R)-ethyl 15-(3-amino-5-methoxyphenyl)-11,12-dimethoxy-2,4,8,10,14-pentamethylpentadeca-2,6,8-trienoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: tert.-butyl lithium / diethyl ether; pentane / 2 h / -78 - 20 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

2.2: 0.25 h / 20 °C / Inert atmosphere

2.3: 0.25 h / 20 °C / Inert atmosphere

3.1: triethyl borane; tri-n-butyl-tin hydride / tetrahydrofuran; toluene / 1 h / 20 °C

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid / dichloromethane / 3 h / 40 °C / Inert atmosphere

5.1: titanium(IV) isopropylate; cyclopentylmagnesium chloride / diethyl ether / 1.5 h / -78 - -30 °C / Inert atmosphere

5.2: 2 h / -78 - -30 °C / Inert atmosphere

With titanium(IV) isopropylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid; triethyl borane; tert.-butyl lithium; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; cyclopentylmagnesium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; pentane; 3.1: Barton deoxygenation;
DOI:10.1021/ol2019828

Reference yield:

: 1332626-21-7
(2S,4S,5R,6S)-1-(3-(diallylamino)-5-methoxyphenyl)-4,5-dimethoxy-2,6-dimethylnon-7-yn-1-ol

: (2E,4R,10S,11R,12S,14R)-ethyl 15-(3-amino-5-methoxyphenyl)-11,12-dimethoxy-2,4,8,10,14-pentamethylpentadeca-2,6,8-trienoate

: 1332626-38-6
(2E,4R,6E,8E,10S,11R,12S,14R)-ethyl 15-(3-amino-5-methoxyphenyl)-11,12-dimethoxy-2,4,8,10,14-pentamethylpentadeca-2,6,8-trienoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

1.2: 0.25 h / 20 °C / Inert atmosphere

1.3: 0.25 h / 20 °C / Inert atmosphere

2.1: triethyl borane; tri-n-butyl-tin hydride / tetrahydrofuran; toluene / 1 h / 20 °C

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid / dichloromethane / 3 h / 40 °C / Inert atmosphere

4.1: titanium(IV) isopropylate; cyclopentylmagnesium chloride / diethyl ether / 1.5 h / -78 - -30 °C / Inert atmosphere

4.2: 2 h / -78 - -30 °C / Inert atmosphere

With titanium(IV) isopropylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid; triethyl borane; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; cyclopentylmagnesium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 2.1: Barton deoxygenation;
DOI:10.1021/ol2019828