(E)-(5S,11S,14S,17R,18R)-11-(3-hydroxybenzyl)-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.1^5,9]octacosa-1⁽²⁷⁾,21,23,25-tetraene-4,10,13,16-tetraone

Base Information

• Chemical Name: (E)-(5S,11S,14S,17R,18R)-11-(3-hydroxybenzyl)-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.1^5,9]octacosa-1⁽²⁷⁾,21,23,25-tetraene-4,10,13,16-tetraone
• CAS No.: 1381808-76-9
• Molecular Formula: C₃₅H₄₆N₄O₇
• Molecular Weight: 634.773

Synonyms:(E)-(5S,11S,14S,17R,18R)-11-(3-hydroxybenzyl)-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.1^5,9]octacosa-1⁽²⁷⁾,21,23,25-tetraene-4,10,13,16-tetraone

Chemical Property of (E)-(5S,11S,14S,17R,18R)-11-(3-hydroxybenzyl)-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.1^5,9]octacosa-1⁽²⁷⁾,21,23,25-tetraene-4,10,13,16-tetraone

Chemical Property:

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Technology Process of (E)-(5S,11S,14S,17R,18R)-11-(3-hydroxybenzyl)-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.1^5,9]octacosa-1⁽²⁷⁾,21,23,25-tetraene-4,10,13,16-tetraone

There total 12 articles about (E)-(5S,11S,14S,17R,18R)-11-(3-hydroxybenzyl)-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.1^5,9]octacosa-1⁽²⁷⁾,21,23,25-tetraene-4,10,13,16-tetraone 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: 44.0%

(E)-(5S,11S,14S,17R,18R)-11-[3-(tert-butyldimethylsilanyloxy)benzyl]-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.15,9]octacosa-1(27),21,23,25-tetraene-4,10,13,16-tetraone (1381816-56-3) → (E)-(5S,11S,14S,17R,18R)-11-(3-hydroxybenzyl)-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.15,9]octacosa-1(27),21,23,25-tetraene-4,10,13,16-tetraone (1381808-76-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h;

DOI:10.1021/acs.jmedchem.6b01329

Reference yield:

3-Ethenylbenzyl alcohol (45804-94-2) → (E)-(5S,11S,14S,17R,18R)-11-(3-hydroxybenzyl)-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.15,9]octacosa-1(27),21,23,25-tetraene-4,10,13,16-tetraone (1381808-76-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran / 6 h / 20 - 40 °C / Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1.5 h / 20 °C

3.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

3.2: 16 h / 0 - 20 °C / Inert atmosphere

4.1: Grubbs catalyst first generation / dichloromethane / 16 h / Reflux

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; sodium hydride; N-ethyl-N,N-diisopropylamine; HATU; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

(S)-1-{(S)-2-((S)-2-amino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid 3-vinylbenzyl ester (1381812-31-2) → (E)-(5S,11S,14S,17R,18R)-11-(3-hydroxybenzyl)-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.15,9]octacosa-1(27),21,23,25-tetraene-4,10,13,16-tetraone (1381808-76-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

1.2: 16 h / 0 - 20 °C / Inert atmosphere

2.1: Grubbs catalyst first generation / dichloromethane / 16 h / Reflux

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

With tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; HATU; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

3-Ethenylbenzyl alcohol

(S)-1-{(S)-2-((S)-2-amino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid 3-vinylbenzyl ester

(E)-(5S,11S,14S,17R,18R)-11-[3-(tert-butyldimethylsilanyloxy)benzyl]-14-isopropyl-18-methoxy-17-methyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.1^5,9]octacosa-1⁽²⁷⁾,21,23,25-tetraene-4,10,13,16-tetraone

(tert-butoxycarbonyl)-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid 2,2,2-trichloroethyl ester

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