Technology Process of (E)-(1S,14R,15R,18S,21S)-21-(3-hydroxy-benzyl)-18-isopropyl-14-methoxy-15-methyl-3-oxa-6,17,20,23,27-pentaaza-tricyclo[21.3.1.1*5,9*]octacosa-5,7,9(28),10-tetraene-2,16,19,22-tetraone
There total 12 articles about (E)-(1S,14R,15R,18S,21S)-21-(3-hydroxy-benzyl)-18-isopropyl-14-methoxy-15-methyl-3-oxa-6,17,20,23,27-pentaaza-tricyclo[21.3.1.1*5,9*]octacosa-5,7,9(28),10-tetraene-2,16,19,22-tetraone which
guide to synthetic route it.
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synthetic route:
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1381809-27-3
(E)-(1S,14R,15R,18S,21S)-21-(3-hydroxy-benzyl)-18-isopropyl-14-methoxy-15-methyl-3-oxa-6,17,20,23,27-pentaaza-tricyclo[21.3.1.1*5,9*]octacosa-5,7,9(28),10-tetraene-2,16,19,22-tetraone
- Guidance literature:
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Multi-step reaction with 6 steps
1.1: triethylamine; calcium hydride; t-butyldimethylsiyl triflate / dichloromethane / 15 h / 20 °C / Inert atmosphere
1.2: 0.5 h / -78 °C / Inert atmosphere
2.1: proton sponge / dichloromethane / 15 h / 20 °C
3.1: water; lithium hydroxide / tetrahydrofuran / 15 h / 60 °C
4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 4 h / 20 °C
5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / 1,2-dichloro-ethane / 3 h / 80 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere
With
calcium hydride; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium hydroxide;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride;
In
tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; acetonitrile;
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1381809-27-3
(E)-(1S,14R,15R,18S,21S)-21-(3-hydroxy-benzyl)-18-isopropyl-14-methoxy-15-methyl-3-oxa-6,17,20,23,27-pentaaza-tricyclo[21.3.1.1*5,9*]octacosa-5,7,9(28),10-tetraene-2,16,19,22-tetraone
- Guidance literature:
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Multi-step reaction with 6 steps
1.1: bis-triphenylphosphine-palladium(II) chloride / toluene / 36 h / 50 - 80 °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 / 4 h / 20 °C
5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / 1,2-dichloro-ethane / 3 h / 80 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere
With
dmap; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; 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;
In
tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; toluene; acetonitrile;
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1381809-27-3
(E)-(1S,14R,15R,18S,21S)-21-(3-hydroxy-benzyl)-18-isopropyl-14-methoxy-15-methyl-3-oxa-6,17,20,23,27-pentaaza-tricyclo[21.3.1.1*5,9*]octacosa-5,7,9(28),10-tetraene-2,16,19,22-tetraone
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: ethanol; sodium tetrahydroborate / 18 h / 20 °C / Inert atmosphere
2.1: bis-triphenylphosphine-palladium(II) chloride / toluene / 36 h / 50 - 80 °C / Inert atmosphere
3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 20 °C
4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / Inert atmosphere
4.2: 0 °C / Inert atmosphere
5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 4 h / 20 °C
6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / 1,2-dichloro-ethane / 3 h / 80 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere
With
dmap; sodium tetrahydroborate; ethanol; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; 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;
In
tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; toluene; acetonitrile;