(E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-9-ene-4-carboxylic acid

Base Information

• Chemical Name: (E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-9-ene-4-carboxylic acid
• CAS No.: 300832-05-7
• Molecular Formula: C₃₉H₄₆N₄O₉
• Molecular Weight: 714.816

Synonyms:(E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-9-ene-4-carboxylic acid

Chemical Property of (E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-9-ene-4-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-9-ene-4-carboxylic acid

There total 6 articles about (E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-9-ene-4-carboxylic acid 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:

(E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-9-ene-4-carboxylic acid methyl ester (300831-66-7) → (E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-9-ene-4-carboxylic acid (300832-05-7)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃;

DOI:10.1016/j.jorganchem.2006.09.027

Reference yield:

(2S,3R)-3-Allyloxy-2-tert-butoxycarbonylamino-butyric acid methyl ester (300831-36-1) → (E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-9-ene-4-carboxylic acid (300832-05-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 200 mg / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 2 h / 20 °C

2: 32 percent / DIPEA; HATU / dimethylformamide / 20 h / 20 °C

3: 41 percent / bis(tricyclohexylphosphine)benzylidene Ru(IV) dichloride / CH₂Cl₂ / 2 h / Heating

4: LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 20 °C

With lithium hydroxide; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.jorganchem.2006.09.027

Reference yield:

Boc-Thr(All)-OH (300831-37-2) → (E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-9-ene-4-carboxylic acid (300832-05-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 32 percent / DIPEA; HATU / dimethylformamide / 20 h / 20 °C

2: 41 percent / bis(tricyclohexylphosphine)benzylidene Ru(IV) dichloride / CH₂Cl₂ / 2 h / Heating

3: LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 20 °C

With lithium hydroxide; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.jorganchem.2006.09.027

upstream raw materials:

(E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-9-ene-4-carboxylic acid methyl ester

Boc-Thr(All)-OH

(2S,3R)-3-Allyloxy-2-tert-butoxycarbonylamino-butyric acid methyl ester

(1R,2R)-1-{[(2S,4R)-1-((2S,3R)-3-Allyloxy-2-tert-butoxycarbonylamino-butyryl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-but-3-enyl-cyclopropanecarboxylic acid methyl ester

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