(8R,11R,14S)-11-(3,5-Dichloro-4-methoxy-phenyl)-4-methoxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester

Base Information

• Chemical Name: (8R,11R,14S)-11-(3,5-Dichloro-4-methoxy-phenyl)-4-methoxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester
• CAS No.: 586413-69-6
• Molecular Formula: C₃₁H₂₈Cl₂F₃N₃O₈
• Molecular Weight: 698.48

Synonyms:(8R,11R,14S)-11-(3,5-Dichloro-4-methoxy-phenyl)-4-methoxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester

Chemical Property of (8R,11R,14S)-11-(3,5-Dichloro-4-methoxy-phenyl)-4-methoxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (8R,11R,14S)-11-(3,5-Dichloro-4-methoxy-phenyl)-4-methoxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester

There total 11 articles about (8R,11R,14S)-11-(3,5-Dichloro-4-methoxy-phenyl)-4-methoxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester 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:

isovanillin (621-59-0) → (8R,11R,14S)-11-(3,5-Dichloro-4-methoxy-phenyl)-4-methoxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3(21),4,6,16(20),17-hexaene-14-carboxylic acid methyl ester (586413-69-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / imidazole / dimethylformamide / 0.5 h

2: 98 percent / MgSO₄ / benzene / 24 h

3: Ti(O-i-Pr)4; chiral amino acid ligand; isopropanol / toluene / 4 h

4: 3.11 g / NaHCO₃; 1-hydroxy-7-azabenzotriazole; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide / tetrahydrofuran; dimethylformamide / 12 h / 22 °C

5: NH₄OAc; aq. NaIO₄ / acetone / 12 h / 22 °C

6: 650 mg / Cu(OAc)2; 4A molecular sieves; Et₃N / CH₂Cl₂; methanol / 6 h / 22 °C

7: 98 percent / HCl / methanol / 1.5 h / 22 °C

8: 860 mg / 2,6-lutidine / CH₂Cl₂ / 2 h

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; sodium periodate; 1-hydroxy-7-aza-benzotriazole; copper diacetate; 4 A molecular sieve; chiral amino acid ligand; ammonium acetate; sodium hydrogencarbonate; magnesium sulfate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; isopropyl alcohol; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1021/ja030249r

Reference yield:

p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde (97315-18-9) → (8R,11R,14S)-11-(3,5-Dichloro-4-methoxy-phenyl)-4-methoxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3(21),4,6,16(20),17-hexaene-14-carboxylic acid methyl ester (586413-69-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / MgSO₄ / benzene / 24 h

2: Ti(O-i-Pr)4; chiral amino acid ligand; isopropanol / toluene / 4 h

3: 3.11 g / NaHCO₃; 1-hydroxy-7-azabenzotriazole; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide / tetrahydrofuran; dimethylformamide / 12 h / 22 °C

4: NH₄OAc; aq. NaIO₄ / acetone / 12 h / 22 °C

5: 650 mg / Cu(OAc)2; 4A molecular sieves; Et₃N / CH₂Cl₂; methanol / 6 h / 22 °C

6: 98 percent / HCl / methanol / 1.5 h / 22 °C

7: 860 mg / 2,6-lutidine / CH₂Cl₂ / 2 h

With 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; sodium periodate; 1-hydroxy-7-aza-benzotriazole; copper diacetate; 4 A molecular sieve; chiral amino acid ligand; ammonium acetate; sodium hydrogencarbonate; magnesium sulfate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; isopropyl alcohol; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1021/ja030249r

Reference yield:

(R)-N-Boc-m-hydroxy-p-methoxyphenyl-Gly (391213-72-2) → (8R,11R,14S)-11-(3,5-Dichloro-4-methoxy-phenyl)-4-methoxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3(21),4,6,16(20),17-hexaene-14-carboxylic acid methyl ester (586413-69-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 3.11 g / NaHCO₃; 1-hydroxy-7-azabenzotriazole; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide / tetrahydrofuran; dimethylformamide / 12 h / 22 °C

2: NH₄OAc; aq. NaIO₄ / acetone / 12 h / 22 °C

3: 650 mg / Cu(OAc)2; 4A molecular sieves; Et₃N / CH₂Cl₂; methanol / 6 h / 22 °C

4: 98 percent / HCl / methanol / 1.5 h / 22 °C

5: 860 mg / 2,6-lutidine / CH₂Cl₂ / 2 h

With 2,6-dimethylpyridine; hydrogenchloride; sodium periodate; 1-hydroxy-7-aza-benzotriazole; copper diacetate; 4 A molecular sieve; ammonium acetate; sodium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja030249r

upstream raw materials:

trifluoroacetic anhydride

(8R,11R,14S)-8-Amino-11-(3,5-dichloro-4-methoxy-phenyl)-4-methoxy-13-methyl-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester

isovanillin

p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde

Downstream raw materials:

(R)-{[(8R,11R,14S)-8-Amino-11-(3,5-dichloro-4-hydroxy-phenyl)-4-hydroxy-5-iodo-13-methyl-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carbonyl]-amino}-(4-hydroxy-phenyl)-acetic acid methyl ester

C₄₃H₄₅Cl₂F₃N₄O₁₀Si

C₄₃H₄₄Cl₂F₃IN₄O₁₀Si

C₄₈H₄₄Cl₄IN₅O₁₃

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