(8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid methylamide

Base Information

• Chemical Name: (8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid methylamide
• CAS No.: 391213-82-4
• Molecular Formula: C₃₀H₂₇F₄N₅O₉
• Molecular Weight: 677.566

Synonyms:(8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid methylamide

Chemical Property of (8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid methylamide

Chemical Property:

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Technology Process of (8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid methylamide

There total 22 articles about (8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid methylamide 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:

4-fluoro-3-nitrobenzaldehyde (42564-51-2) → (8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.13,7]icosa-1(18),3(20),4,6,15(19),16-hexaene-8-carboxylic acid methylamide (391213-82-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 99 percent / TMG / tetrahydrofuran

2.1: H₂; chiral Rh(I) complex / tetrahydrofuran / 20 °C / 760.05 Torr

3.1: DMAP / tetrahydrofuran / 20 °C

3.2: 88 percent / N₂H₄ / methanol / 20 °C

4.1: TFA; DMS / CH₂Cl₂ / 0 °C

5.1: 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 0 - 20 °C

6.1: TFA; DMS / CH₂Cl₂ / 0 °C

7.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

8.1: 80 percent / Cu(OAc)2; pyridine; O₂ / CH₂Cl₂ / 20 °C

9.1: 99 percent / LiOH / methanol; H₂O / 0 °C

10.1: TFA; DMS / CH₂Cl₂ / 0 °C

11.1: HATU; HOAt / CH₂Cl₂; dimethylformamide / 0 - 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; copper diacetate; 2,3-dimercapto-succinic acid; hydrogen; oxygen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja011943e

Reference yield:

(R)-2-[(R)-2-{3-[3-((S)-Amino-methylcarbamoyl-methyl)-5-methoxy-phenoxy]-4-methoxy-phenyl}-2-(2,2,2-trifluoro-acetylamino)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid → (8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.13,7]icosa-1(18),3(20),4,6,15(19),16-hexaene-8-carboxylic acid methylamide (391213-82-4)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/ja011943e

Reference yield:

2-(3-benzyloxy-4-methoxyphenyl)ethylene (68360-39-4) → (8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.13,7]icosa-1(18),3(20),4,6,15(19),16-hexaene-8-carboxylic acid methylamide (391213-82-4)

Guidance literature:

Multi-step reaction with 10 steps

1: K₂OsO₂(OH)4; (DHQD)2PHAL / propan-1-ol; H₂O

2: TEMPO; NaOCl; KBr / acetone; H₂O

3: 100 percent / H₂ / Pd/C / ethanol / 760.05 Torr

4: 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 0 - 20 °C

5: TFA; DMS / CH₂Cl₂ / 0 °C

6: 2,6-lutidine / CH₂Cl₂ / 0 °C

7: 80 percent / Cu(OAc)2; pyridine; O₂ / CH₂Cl₂ / 20 °C

8: 99 percent / LiOH / methanol; H₂O / 0 °C

9: TFA; DMS / CH₂Cl₂ / 0 °C

10: HATU; HOAt / CH₂Cl₂; dimethylformamide / 0 - 20 °C

With pyridine; 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; sodium hypochlorite; 1-hydroxy-7-aza-benzotriazole; copper diacetate; potassium dioxotetrahydroxoosmate(VI); 2,3-dimercapto-succinic acid; hydrogen; oxygen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,4-bis(9-O-dihydroquinidine)phthalazine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; propan-1-ol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; 1: Sharpless asymmetric amino-hydroxylation;

DOI:10.1021/ja011943e

upstream raw materials:

2-(3-benzyloxy-4-methoxyphenyl)ethylene

4-fluoro-3-nitrobenzaldehyde

D-(4-fluoro-3-nitrophenyl)glycine methyl ester

(R)-N-(tert-butoxycarbonyl)-4-fluoro-3-nitrophenylalanine methyl ester

Downstream raw materials:

(8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid

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