2-benzyloxyimino-3-{3-[4-(2-benzyloxyimino-2-tert-butoxycarbonyl-ethyl)-2-bromo-phenoxy]-5-bromo-4-tert-butoxycarbonyloxy-phenyl}-propionic acid

Base Information

• Chemical Name: 2-benzyloxyimino-3-{3-[4-(2-benzyloxyimino-2-tert-butoxycarbonyl-ethyl)-2-bromo-phenoxy]-5-bromo-4-tert-butoxycarbonyloxy-phenyl}-propionic acid
• CAS No.: 845784-16-9
• Molecular Formula: C₄₁H₄₂Br₂N₂O₁₀
• Molecular Weight: 882.6
• Mol file: 845784-16-9.mol

Synonyms:2-benzyloxyimino-3-{3-[4-(2-benzyloxyimino-2-tert-butoxycarbonyl-ethyl)-2-bromo-phenoxy]-5-bromo-4-tert-butoxycarbonyloxy-phenyl}-propionic acid

Chemical Property of 2-benzyloxyimino-3-{3-[4-(2-benzyloxyimino-2-tert-butoxycarbonyl-ethyl)-2-bromo-phenoxy]-5-bromo-4-tert-butoxycarbonyloxy-phenyl}-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzyloxyimino-3-{3-[4-(2-benzyloxyimino-2-tert-butoxycarbonyl-ethyl)-2-bromo-phenoxy]-5-bromo-4-tert-butoxycarbonyloxy-phenyl}-propionic acid

There total 17 articles about 2-benzyloxyimino-3-{3-[4-(2-benzyloxyimino-2-tert-butoxycarbonyl-ethyl)-2-bromo-phenoxy]-5-bromo-4-tert-butoxycarbonyloxy-phenyl}-propionic 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: 85.0%

2-benzyloxyimino-3-{3-[4-(2-benzyloxyimino-2-tert-butoxycarbonyl-ethyl)-2-bromo-phenoxy]-5-bromo-4-tert-butoxycarbonyloxy-phenyl}-propionic acid methyl ester (845784-15-8) → 2-benzyloxyimino-3-{3-[4-(2-benzyloxyimino-2-tert-butoxycarbonyl-ethyl)-2-bromo-phenoxy]-5-bromo-4-tert-butoxycarbonyloxy-phenyl}-propionic acid (845784-16-9)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; at 0 ℃;

DOI:10.1002/chem.200400904

Reference yield:

4-benzyloxy-3-[2-bromo-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenoxy]-benzaldehyde (705932-29-2) → 2-benzyloxyimino-3-{3-[4-(2-benzyloxyimino-2-tert-butoxycarbonyl-ethyl)-2-bromo-phenoxy]-5-bromo-4-tert-butoxycarbonyloxy-phenyl}-propionic acid (845784-16-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 99 percent / piperidine; Ac₂O / tetrahydrofuran / 24 h / 80 °C

2.1: 86 percent / NaBH₄ / methanol; acetonitrile / 4 h / 0 - 20 °C

3.1: 88 percent / NaOMe; BuONO / methanol / 48 h / 0 °C

4.1: imidazole; K₂CO₃ / dimethylformamide / 0.5 h / 0 °C

4.2: 91 percent / dimethylformamide / 12 h / 0 - 20 °C

5.1: 99 percent / aq. HCl / tetrahydrofuran / 20 °C

6.1: 88 percent / imidazole / dimethylformamide / 11 h / 0 - 20 °C

7.1: TEMPO; KBr; aq. NaOCl / NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

8.1: pyridine / ethanol / 20 °C

9.1: 24 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

10.1: 97 percent / TEMPO; aq. KBr; NaOCl / NaHCO₃ / acetonitrile / 2 h / 0 °C

11.1: 94 percent / TFA; pentamethylbenzene / 2.5 h / 0 - 20 °C

12.1: 100 percent / NBS / acetonitrile / 1 h / 0 °C

13.1: 81 percent / DMAP / tetrahydrofuran / 12 h / 0 °C

14.1: 85 percent / aq. NaOH / methanol; tetrahydrofuran / 0 °C

With piperidine; pyridine; 1H-imidazole; hydrogenchloride; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide; sodium hypochlorite; sodium tetrahydroborate; N-Bromosuccinimide; n-Butyl nitrite; pentamethylbenzene,; tetrabutyl ammonium fluoride; sodium methylate; acetic anhydride; potassium carbonate; trifluoroacetic acid; potassium bromide; sodium hydrogencarbonate; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Knoevenagel condensation;

DOI:10.1002/chem.200400904

Reference yield:

2-{4-benzyloxy-3-[2-bromo-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenoxy]-benzylidene}-malonic acid dimethyl ester (845784-02-3) → 2-benzyloxyimino-3-{3-[4-(2-benzyloxyimino-2-tert-butoxycarbonyl-ethyl)-2-bromo-phenoxy]-5-bromo-4-tert-butoxycarbonyloxy-phenyl}-propionic acid (845784-16-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 86 percent / NaBH₄ / methanol; acetonitrile / 4 h / 0 - 20 °C

2.1: 88 percent / NaOMe; BuONO / methanol / 48 h / 0 °C

3.1: imidazole; K₂CO₃ / dimethylformamide / 0.5 h / 0 °C

3.2: 91 percent / dimethylformamide / 12 h / 0 - 20 °C

4.1: 99 percent / aq. HCl / tetrahydrofuran / 20 °C

5.1: 88 percent / imidazole / dimethylformamide / 11 h / 0 - 20 °C

6.1: TEMPO; KBr; aq. NaOCl / NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

7.1: pyridine / ethanol / 20 °C

8.1: 24 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

9.1: 97 percent / TEMPO; aq. KBr; NaOCl / NaHCO₃ / acetonitrile / 2 h / 0 °C

10.1: 94 percent / TFA; pentamethylbenzene / 2.5 h / 0 - 20 °C

11.1: 100 percent / NBS / acetonitrile / 1 h / 0 °C

12.1: 81 percent / DMAP / tetrahydrofuran / 12 h / 0 °C

13.1: 85 percent / aq. NaOH / methanol; tetrahydrofuran / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide; sodium hypochlorite; sodium tetrahydroborate; N-Bromosuccinimide; n-Butyl nitrite; pentamethylbenzene,; tetrabutyl ammonium fluoride; sodium methylate; potassium carbonate; trifluoroacetic acid; potassium bromide; sodium hydrogencarbonate; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/chem.200400904

upstream raw materials:

2-benzyloxyimino-3-{3-[4-(2-benzyloxyimino-2-tert-butoxycarbonyl-ethyl)-2-bromo-phenoxy]-5-bromo-4-tert-butoxycarbonyloxy-phenyl}-propionic acid methyl ester

4-benzyloxy-3-[2-bromo-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenoxy]-benzaldehyde

2-{4-benzyloxy-3-[2-bromo-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenoxy]-benzylidene}-malonic acid dimethyl ester

2-{4-benzyloxy-3-[2-bromo-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenoxy]-benzyl}-malonic acid dimethyl ester

Downstream raw materials:

C₄₈H₄₁Br₃N₄O₈

C₄₈H₄₀Br₄N₄O₈

bastadin 20

2-benzyloxyimino-3-(4-{5-[2-benzyloxyimino-2-(2-{3-[2-bromo-4-(2-tert-butoxycarbonylamino-ethyl)-phenoxy]-4-hydroxy-phenyl}-ethylcarbamoyl)-ethyl]-3-bromo-2-tert-butoxycarbonyloxy-phenoxy}-3-bromo-phenyl)-propionic acid tert-butyl ester