(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

Base Information

• Chemical Name: (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
• CAS No.: 586413-72-1
• Molecular Formula: C₃₅H₃₁Cl₂IN₄O₉
• Molecular Weight: 849.463

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 19 articles about (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 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:

C43H44Cl2F3IN4O10Si (586413-71-0) → (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[14.2.2.13,7]henicosa-1(19),3(21),4,6,16(20),17-hexaene-14-carbonyl]-amino}-(4-hydroxy-phenyl)-acetic acid methyl ester (586413-72-1)

Guidance literature:

With hydrogenchloride; In methanol; at 45 ℃; for 5h;

DOI:10.1021/ja030249r

Reference yield:

C40H39Cl2IN4O11 (1042907-20-9) → (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[14.2.2.13,7]henicosa-1(19),3(21),4,6,16(20),17-hexaene-14-carbonyl]-amino}-(4-hydroxy-phenyl)-acetic acid methyl ester (586413-72-1)

Guidance literature:

C₄₀H₃₉Cl₂IN₄O₁₁; With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1h;

With sodium hydrogencarbonate; In water;

DOI:10.1002/anie.200800599

Reference yield:

isovanillin (621-59-0) → (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[14.2.2.13,7]henicosa-1(19),3(21),4,6,16(20),17-hexaene-14-carbonyl]-amino}-(4-hydroxy-phenyl)-acetic acid methyl ester (586413-72-1)

Guidance literature:

Multi-step reaction with 13 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

9: 1.0 g / AlBr₃; EtSH / 1.5 h / 0 °C

10: 940 mg / 1-hydroxy-7-azabenzotriazole; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide; NaHCO₃ / tetrahydrofuran / 12 h / 22 °C

11: 390 mg / NIS / acetonitrile / 0.42 h / 22 °C

12: 85 mg / HCl / methanol / 5 h / 45 °C

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

DOI:10.1021/ja030249r

upstream raw materials:

C₄₃H₄₄Cl₂F₃IN₄O₁₀Si

isovanillin

(R)-methyl 2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate

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

Downstream raw materials:

C₄₈H₄₄Cl₄IN₅O₁₃

C₅₉H₅₃Cl₄N₇O₁₄

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