6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-2-{[2-(2-hydroxy-5-methoxy-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-hexanoic acid 1-{1-[1-(tert-butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-ylcarbamoyl]-1-methyl-ethyl}-octyl ester

Base Information

• Chemical Name: 6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-2-{[2-(2-hydroxy-5-methoxy-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-hexanoic acid 1-{1-[1-(tert-butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-ylcarbamoyl]-1-methyl-ethyl}-octyl ester
• CAS No.: 284470-02-6
• Molecular Formula: C₅₉H₈₇N₅O₁₂Si₂
• Molecular Weight: 1114.54

Synonyms:6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-2-{[2-(2-hydroxy-5-methoxy-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-hexanoic acid 1-{1-[1-(tert-butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-ylcarbamoyl]-1-methyl-ethyl}-octyl ester

Chemical Property of 6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-2-{[2-(2-hydroxy-5-methoxy-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-hexanoic acid 1-{1-[1-(tert-butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-ylcarbamoyl]-1-methyl-ethyl}-octyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-2-{[2-(2-hydroxy-5-methoxy-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-hexanoic acid 1-{1-[1-(tert-butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-ylcarbamoyl]-1-methyl-ethyl}-octyl ester

There total 22 articles about 6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-2-{[2-(2-hydroxy-5-methoxy-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-hexanoic acid 1-{1-[1-(tert-butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-ylcarbamoyl]-1-methyl-ethyl}-octyl 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:

5-methoxysalicylic acid (2612-02-4) → 6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-2-{[2-(2-hydroxy-5-methoxy-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-hexanoic acid 1-{1-[1-(tert-butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-ylcarbamoyl]-1-methyl-ethyl}-octyl ester (284470-02-6)

Guidance literature:

Multi-step reaction with 8 steps

1: K₂CO₃ / dimethylformamide / 21.5 h / 0 - 20 °C

2: 2.15 g / aq. NaOH / methanol / 1 h / 20 °C

3: 98 percent / DEPC; Et₃N / dimethylformamide / 12 h / 0 - 20 °C

4: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

5: 146 mg / PPh₃; Et₃N; Cl₃CCCl₃ / CH₂Cl₂ / 0.5 h / -10 °C

6: H₂ / Pd/C / methanol / 2.5 h / 20 °C / 760 Torr

7: 85 percent / aq. NaOH / tetrahydrofuran / 1.25 h / 20 °C

8: 16 mg / EDCI*HCl / CH₂Cl₂ / 2 h / 20 °C

With sodium hydroxide; hexachloroethane; hydrogen; potassium carbonate; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; diethyl dicarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Hydrolysis / 3: Acylation / 4: Oxidation / 5: Cyclization / 6: Hydrogenolysis / 7: Hydrolysis / 8: Condensation;

DOI:10.1016/S0040-4020(00)00170-8

Reference yield:

Octanal (124-13-0) → 6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-2-{[2-(2-hydroxy-5-methoxy-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-hexanoic acid 1-{1-[1-(tert-butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-ylcarbamoyl]-1-methyl-ethyl}-octyl ester (284470-02-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 54 percent / N-tosyl-D-Val-OH; BH₃*THF / tetrahydrofuran / 1 h / -78 °C

2: 93 percent / aq. NaOH / methanol / 3.5 h / 20 °C

3: 32 mg / DEPC; DIPEA / dimethylformamide / 4.5 h / 0 - 20 °C

4: 34 mg / DCC; DMAP / toluene / 39 h / 20 °C

5: H₂ / Pd/C / methanol / 2 h / 20 °C / 760 Torr

6: 16 mg / EDCI*HCl / CH₂Cl₂ / 2 h / 20 °C

With dmap; sodium hydroxide; borane-THF; N-((4-methylphenyl)sulfonyl)-D-valine; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; diethyl dicarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: aldol reaction / 2: Hydrolysis / 3: Condensation / 4: Condensation / 5: Hydrogenolysis / 6: Condensation;

DOI:10.1016/S0040-4020(00)00170-8

Reference yield:

2-(benzyloxy)-5-methoxybenzoic acid (53985-53-8) → 6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-2-{[2-(2-hydroxy-5-methoxy-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-hexanoic acid 1-{1-[1-(tert-butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-ylcarbamoyl]-1-methyl-ethyl}-octyl ester (284470-02-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / DEPC; Et₃N / dimethylformamide / 12 h / 0 - 20 °C

2: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

3: 146 mg / PPh₃; Et₃N; Cl₃CCCl₃ / CH₂Cl₂ / 0.5 h / -10 °C

4: H₂ / Pd/C / methanol / 2.5 h / 20 °C / 760 Torr

5: 85 percent / aq. NaOH / tetrahydrofuran / 1.25 h / 20 °C

6: 16 mg / EDCI*HCl / CH₂Cl₂ / 2 h / 20 °C

With sodium hydroxide; hexachloroethane; hydrogen; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; diethyl dicarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Oxidation / 3: Cyclization / 4: Hydrogenolysis / 5: Hydrolysis / 6: Condensation;

DOI:10.1016/S0040-4020(00)00170-8

upstream raw materials:

2-[(2-hydroxy-5-methoxy)phenyl]-5-methyloxazole-4-caboxylic acid

(R)-2-Amino-6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-hexanoic acid (S)-1-{1-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-ylcarbamoyl]-1-methyl-ethyl}-octyl ester

Octanal

5-methoxysalicylic acid

Downstream raw materials:

amamistatin A

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