(2R,5S,11S,14S,17R,18R)-11-(3-hydroxy-benzyl)-14-isopropyl-18-methoxy-2,17-dimethyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁷⁾,23,25-triene-4,10,13,16-tetraone

Base Information

• Chemical Name: (2R,5S,11S,14S,17R,18R)-11-(3-hydroxy-benzyl)-14-isopropyl-18-methoxy-2,17-dimethyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁷⁾,23,25-triene-4,10,13,16-tetraone
• CAS No.: 1381809-56-8
• Molecular Formula: C₃₆H₅₀N₄O₇
• Molecular Weight: 650.816

Synonyms:(2R,5S,11S,14S,17R,18R)-11-(3-hydroxy-benzyl)-14-isopropyl-18-methoxy-2,17-dimethyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁷⁾,23,25-triene-4,10,13,16-tetraone

Chemical Property of (2R,5S,11S,14S,17R,18R)-11-(3-hydroxy-benzyl)-14-isopropyl-18-methoxy-2,17-dimethyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁷⁾,23,25-triene-4,10,13,16-tetraone

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Technology Process of (2R,5S,11S,14S,17R,18R)-11-(3-hydroxy-benzyl)-14-isopropyl-18-methoxy-2,17-dimethyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁷⁾,23,25-triene-4,10,13,16-tetraone

There total 12 articles about (2R,5S,11S,14S,17R,18R)-11-(3-hydroxy-benzyl)-14-isopropyl-18-methoxy-2,17-dimethyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁷⁾,23,25-triene-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: 47.0%

(E)-(2R,5S,11S,14S,17R,18R)-11-(3-hydroxybenzyl)-14-isopropyl-18-methoxy-2,17-dimethyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.15,9]octacosa-1(26),21,23(27),24-tetraene-4,10,13,16-tetraone (1381809-07-9) → (2R,5S,11S,14S,17R,18R)-11-(3-hydroxy-benzyl)-14-isopropyl-18-methoxy-2,17-dimethyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1(27),23,25-triene-4,10,13,16-tetraone (1381809-56-8)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In ethyl acetate; at 20 ℃; for 1h; under 760.051 Torr;

Reference yield:

(R)-1-(3-bromophenyl)ethanol (52780-14-0,64382-14-5,134615-22-8,134615-24-0) → (2R,5S,11S,14S,17R,18R)-11-(3-hydroxy-benzyl)-14-isopropyl-18-methoxy-2,17-dimethyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1(27),23,25-triene-4,10,13,16-tetraone (1381809-56-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: bis-triphenylphosphine-palladium(II) chloride / toluene / 36 h / 45 °C / Inert atmosphere

2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 20 °C

3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 18 h / 20 °C

5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / 1,1-dichloroethane / 3 h / Reflux; Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

7.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 1 h / 20 °C / 760.05 Torr

With dmap; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; bis-triphenylphosphine-palladium(II) chloride; palladium 10% on activated carbon; In tetrahydrofuran; 1,1-dichloroethane; dichloromethane; ethyl acetate; toluene; acetonitrile;

Reference yield:

(S)-1-{(S)-2-((S)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid (R)-1-(3-vinylphenyl)ethyl ester (1381812-75-4) → (2R,5S,11S,14S,17R,18R)-11-(3-hydroxy-benzyl)-14-isopropyl-18-methoxy-2,17-dimethyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1(27),23,25-triene-4,10,13,16-tetraone (1381809-56-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 18 h / 20 °C

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / 1,1-dichloroethane / 3 h / Reflux; Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

5.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 1 h / 20 °C / 760.05 Torr

With trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium 10% on activated carbon; In tetrahydrofuran; 1,1-dichloroethane; dichloromethane; ethyl acetate; acetonitrile;

upstream raw materials:

(R)-1-(3-bromophenyl)ethanol

(E)-(2R,5S,11S,14S,17R,18R)-11-(3-hydroxybenzyl)-14-isopropyl-18-methoxy-2,17-dimethyl-3-oxa-9,12,15,28-tetraazatricyclo[21.3.1.1^5,9]octacosa-1⁽²⁶⁾,21,23⁽²⁷⁾,24-tetraene-4,10,13,16-tetraone

(R)-1-(3-vinylphenyl)ethanol

(S)-1-{(S)-2-((S)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid (R)-1-(3-vinylphenyl)ethyl ester

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