(R)-2-[(R)-2-{3-[3-((S)-tert-Butoxycarbonylamino-methylcarbamoyl-methyl)-5-methoxy-phenoxy]-4-methoxy-phenyl}-2-(2,2,2-trifluoro-acetylamino)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

Base Information

• Chemical Name: (R)-2-[(R)-2-{3-[3-((S)-tert-Butoxycarbonylamino-methylcarbamoyl-methyl)-5-methoxy-phenoxy]-4-methoxy-phenyl}-2-(2,2,2-trifluoro-acetylamino)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester
• CAS No.: 391213-78-8
• Molecular Formula: C₃₆H₃₉F₄N₅O₁₂
• Molecular Weight: 809.726

Synonyms:(R)-2-[(R)-2-{3-[3-((S)-tert-Butoxycarbonylamino-methylcarbamoyl-methyl)-5-methoxy-phenoxy]-4-methoxy-phenyl}-2-(2,2,2-trifluoro-acetylamino)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

Chemical Property of (R)-2-[(R)-2-{3-[3-((S)-tert-Butoxycarbonylamino-methylcarbamoyl-methyl)-5-methoxy-phenoxy]-4-methoxy-phenyl}-2-(2,2,2-trifluoro-acetylamino)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (R)-2-[(R)-2-{3-[3-((S)-tert-Butoxycarbonylamino-methylcarbamoyl-methyl)-5-methoxy-phenoxy]-4-methoxy-phenyl}-2-(2,2,2-trifluoro-acetylamino)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

There total 18 articles about (R)-2-[(R)-2-{3-[3-((S)-tert-Butoxycarbonylamino-methylcarbamoyl-methyl)-5-methoxy-phenoxy]-4-methoxy-phenyl}-2-(2,2,2-trifluoro-acetylamino)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic 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:

4-fluoro-3-nitrobenzaldehyde (42564-51-2) → (R)-2-[(R)-2-{3-[3-((S)-tert-Butoxycarbonylamino-methylcarbamoyl-methyl)-5-methoxy-phenoxy]-4-methoxy-phenyl}-2-(2,2,2-trifluoro-acetylamino)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester (391213-78-8)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; 2,6-dimethylpyridine; dmap; 1-hydroxy-7-aza-benzotriazole; copper diacetate; 2,3-dimercapto-succinic acid; hydrogen; oxygen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja011943e

Reference yield:

2-(3-benzyloxy-4-methoxyphenyl)ethylene (68360-39-4) → (R)-2-[(R)-2-{3-[3-((S)-tert-Butoxycarbonylamino-methylcarbamoyl-methyl)-5-methoxy-phenoxy]-4-methoxy-phenyl}-2-(2,2,2-trifluoro-acetylamino)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester (391213-78-8)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; 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; potassium bromide; palladium on activated charcoal; In tetrahydrofuran; propan-1-ol; ethanol; dichloromethane; water; acetone; 1: Sharpless asymmetric amino-hydroxylation;

DOI:10.1021/ja011943e

Reference yield:

3-benzyloxy-4-methoxybenzaldehyde (6346-05-0) → (R)-2-[(R)-2-{3-[3-((S)-tert-Butoxycarbonylamino-methylcarbamoyl-methyl)-5-methoxy-phenoxy]-4-methoxy-phenyl}-2-(2,2,2-trifluoro-acetylamino)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester (391213-78-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 96 percent / KHMDS / tetrahydrofuran

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

3: TEMPO; NaOCl; KBr / acetone; H₂O

4: 100 percent / H₂ / Pd/C / ethanol / 760.05 Torr

5: 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 0 - 20 °C

6: TFA; DMS / CH₂Cl₂ / 0 °C

7: 2,6-lutidine / CH₂Cl₂ / 0 °C

8: 80 percent / Cu(OAc)2; pyridine; O₂ / CH₂Cl₂ / 20 °C

With pyridine; 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; 1-hydroxy-7-aza-benzotriazole; copper diacetate; potassium dioxotetrahydroxoosmate(VI); 2,3-dimercapto-succinic acid; hydrogen; oxygen; potassium hexamethylsilazane; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,4-bis(9-O-dihydroquinidine)phthalazine; trifluoroacetic acid; potassium bromide; palladium on activated charcoal; In tetrahydrofuran; propan-1-ol; ethanol; dichloromethane; water; acetone; 1: Wittig olefination / 2: Sharpless asymmetric amino-hydroxylation;

DOI:10.1021/ja011943e

upstream raw materials:

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

4-fluoro-3-nitrobenzaldehyde

N-chloro-N-sodio-tert-butylcarbamate

D-(4-fluoro-3-nitrophenyl)glycine 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 methylamide

(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

(R)-2-[(R)-2-{3-[3-((S)-tert-Butoxycarbonylamino-methylcarbamoyl-methyl)-5-methoxy-phenoxy]-4-methoxy-phenyl}-2-(2,2,2-trifluoro-acetylamino)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid

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