Acetic acid (R)-2-{[(S)-3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionyl]-[1-(4-methoxy-phenylcarbamoyl)-ethyl]-amino}-2-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl ester

Base Information

• Chemical Name: Acetic acid (R)-2-{[(S)-3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionyl]-[1-(4-methoxy-phenylcarbamoyl)-ethyl]-amino}-2-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl ester
• CAS No.: 442663-48-1
• Molecular Formula: C₄₇H₅₆IN₃O₁₃
• Molecular Weight: 997.878

Synonyms:Acetic acid (R)-2-{[(S)-3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionyl]-[1-(4-methoxy-phenylcarbamoyl)-ethyl]-amino}-2-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl ester

Chemical Property of Acetic acid (R)-2-{[(S)-3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionyl]-[1-(4-methoxy-phenylcarbamoyl)-ethyl]-amino}-2-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl ester

Chemical Property:

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Technology Process of Acetic acid (R)-2-{[(S)-3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionyl]-[1-(4-methoxy-phenylcarbamoyl)-ethyl]-amino}-2-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl ester

There total 28 articles about Acetic acid (R)-2-{[(S)-3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionyl]-[1-(4-methoxy-phenylcarbamoyl)-ethyl]-amino}-2-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl 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: 93.0%

acetic anhydride (108-24-7) + alcohol (442663-47-0) → Acetic acid (R)-2-{[(S)-3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionyl]-[1-(4-methoxy-phenylcarbamoyl)-ethyl]-amino}-2-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl ester (442663-48-1)

Guidance literature:

With pyridine; dmap; at 50 ℃; for 30h;

DOI:10.1021/ja026216d

Reference yield:

Sesamol (533-31-3) → Acetic acid (R)-2-{[(S)-3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionyl]-[1-(4-methoxy-phenylcarbamoyl)-ethyl]-amino}-2-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl ester (442663-48-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: NaH / tetrahydrofuran; dimethylformamide; various solvent(s) / 0 - 20 °C

1.2: 97 percent / tetrahydrofuran; dimethylformamide; various solvent(s) / 0 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0 - 20 °C

2.2: 92 percent / aq. H₂O₂; trimethylboronate; AcOH / tetrahydrofuran; hexane / 4.5 h / 20 °C

3.1: 89 percent / TFA / CH₂Cl₂ / 2.17 h / -10 °C

4.1: 90 percent / pyridine / CH₂Cl₂ / 0.08 h / 0 °C

5.1: 85 percent / NaBH₄ / methanol / 0.5 h / 0 °C

6.1: 91 percent / imidazole / dimethylformamide / 20 °C

7.1: 97 percent / PdCl₂(dppf) / tetrahydrofuran / 4.5 h / Heating

8.1: Pb(OAc)4 / acetonitrile / 0 °C

9.1: 436 mg / NH₂OH*HCl; NaOAc / ethanol / 1.5 h / 20 °C

10.1: 90 percent / methanol / 1 h / Heating

11.1: 89 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

12.1: 93 percent / pyridine; DMAP / 30 h / 50 °C

With pyridine; 1H-imidazole; lead(IV) acetate; dmap; sodium tetrahydroborate; n-butyllithium; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; sodium acetate; sodium hydride; trifluoroacetic acid; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3.1: Mannich reaction / 10.1: Ugi reaction;

DOI:10.1021/ja026216d

Reference yield:

3,4-(methylenedioxy)phenyl methoxymethyl ether (111726-43-3) → Acetic acid (R)-2-{[(S)-3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionyl]-[1-(4-methoxy-phenylcarbamoyl)-ethyl]-amino}-2-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl ester (442663-48-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0 - 20 °C

1.2: 92 percent / aq. H₂O₂; trimethylboronate; AcOH / tetrahydrofuran; hexane / 4.5 h / 20 °C

2.1: 89 percent / TFA / CH₂Cl₂ / 2.17 h / -10 °C

3.1: 90 percent / pyridine / CH₂Cl₂ / 0.08 h / 0 °C

4.1: 85 percent / NaBH₄ / methanol / 0.5 h / 0 °C

5.1: 91 percent / imidazole / dimethylformamide / 20 °C

6.1: 97 percent / PdCl₂(dppf) / tetrahydrofuran / 4.5 h / Heating

7.1: Pb(OAc)4 / acetonitrile / 0 °C

8.1: 436 mg / NH₂OH*HCl; NaOAc / ethanol / 1.5 h / 20 °C

9.1: 90 percent / methanol / 1 h / Heating

10.1: 89 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

11.1: 93 percent / pyridine; DMAP / 30 h / 50 °C

With pyridine; 1H-imidazole; lead(IV) acetate; dmap; sodium tetrahydroborate; n-butyllithium; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; sodium acetate; trifluoroacetic acid; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2.1: Mannich reaction / 9.1: Ugi reaction;

DOI:10.1021/ja026216d

upstream raw materials:

acetic anhydride

alcohol

Sesamol

p-methoxyphenylisonitrile

Downstream raw materials:

C₅₀H₅₈Cl₃N₃O₁₀Si

nitrile compound

3-benzyloxy-11-[1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-2-hydroxy-ethyl]-12-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-13-carboxylic acid 2,2,2-trichloro-ethyl ester

silanylether

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