(E)-(5S,11S,14S,17R,18R)-18-ethoxy-11-(3-hydroxy-benzyl)-14-isopropyl-17-methyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁶⁾,21,23⁽²⁷⁾,24-tetraene-4,10,13,16-tetraone

Base Information

• Chemical Name: (E)-(5S,11S,14S,17R,18R)-18-ethoxy-11-(3-hydroxy-benzyl)-14-isopropyl-17-methyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁶⁾,21,23⁽²⁷⁾,24-tetraene-4,10,13,16-tetraone
• CAS No.: 1381809-93-3
• Molecular Formula: C₃₆H₄₈N₄O₇
• Molecular Weight: 648.8

Synonyms:(E)-(5S,11S,14S,17R,18R)-18-ethoxy-11-(3-hydroxy-benzyl)-14-isopropyl-17-methyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁶⁾,21,23⁽²⁷⁾,24-tetraene-4,10,13,16-tetraone

Chemical Property of (E)-(5S,11S,14S,17R,18R)-18-ethoxy-11-(3-hydroxy-benzyl)-14-isopropyl-17-methyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁶⁾,21,23⁽²⁷⁾,24-tetraene-4,10,13,16-tetraone

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Technology Process of (E)-(5S,11S,14S,17R,18R)-18-ethoxy-11-(3-hydroxy-benzyl)-14-isopropyl-17-methyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁶⁾,21,23⁽²⁷⁾,24-tetraene-4,10,13,16-tetraone

There total 9 articles about (E)-(5S,11S,14S,17R,18R)-18-ethoxy-11-(3-hydroxy-benzyl)-14-isopropyl-17-methyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁶⁾,21,23⁽²⁷⁾,24-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: 53.0%

(E)-(5S,11S,14S,17R,18R)-11-[3-(tert-butyl-dimethyl-silanyloxy)-benzyl]-18-ethoxy-14-isopropyl-17-methyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1(26),21,23(27),24-tetraene-4,10,13,16-tetraone (1381816-16-5) → (E)-(5S,11S,14S,17R,18R)-18-ethoxy-11-(3-hydroxy-benzyl)-14-isopropyl-17-methyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1(26),21,23(27),24-tetraene-4,10,13,16-tetraone (1381809-93-3)

Guidance literature:

(E)-(5S,11S,14S,17R,18R)-11-[3-(tert-butyl-dimethyl-silanyloxy)-benzyl]-18-ethoxy-14-isopropyl-17-methyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁶⁾,21,23⁽²⁷⁾,24-tetraene-4,10,13,16-tetraone; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

With water; sodium hydrogencarbonate; In tetrahydrofuran; Inert atmosphere;

Reference yield:

3-Ethenylbenzyl alcohol (45804-94-2) → (E)-(5S,11S,14S,17R,18R)-18-ethoxy-11-(3-hydroxy-benzyl)-14-isopropyl-17-methyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1(26),21,23(27),24-tetraene-4,10,13,16-tetraone (1381809-93-3)

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 / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

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

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / 1,2-dichloro-ethane / 1.5 h / Reflux

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

5.2: Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; sodium hydride; N-ethyl-N,N-diisopropylamine; HATU; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;

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)-18-ethoxy-11-(3-hydroxy-benzyl)-14-isopropyl-17-methyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1(26),21,23(27),24-tetraene-4,10,13,16-tetraone (1381809-93-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

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

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / 1,2-dichloro-ethane / 1.5 h / Reflux

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.2: Inert atmosphere

With tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; HATU; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;

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

(2R,3R)-3-ethoxy-2-methyl-hept-6-enoic acid

(S)-1-{(S)-3-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-[(S)-2-((2R,3R)-3-ethoxy-2-methyl-hept-6-enoylamino)-3-methyl-butyrylamino]-propionyl}-hexahydro-pyridazine-3-carboxylic acid 3-vinyl-benzyl ester

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