(S)-N-Benzyloxycarbonyl-4-(N-tert-butyloxycarbonyl)aminotryptophan methyl ester

Base Information

• Chemical Name: (S)-N-Benzyloxycarbonyl-4-(N-tert-butyloxycarbonyl)aminotryptophan methyl ester
• CAS No.: 252289-08-0
• Molecular Formula: C₂₅H₂₉N₃O₆
• Molecular Weight: 467.522

Synonyms:(S)-N-Benzyloxycarbonyl-4-(N-tert-butyloxycarbonyl)aminotryptophan methyl ester

Chemical Property of (S)-N-Benzyloxycarbonyl-4-(N-tert-butyloxycarbonyl)aminotryptophan methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-Benzyloxycarbonyl-4-(N-tert-butyloxycarbonyl)aminotryptophan methyl ester

There total 11 articles about (S)-N-Benzyloxycarbonyl-4-(N-tert-butyloxycarbonyl)aminotryptophan 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:

1-(N-triisopropylsilyl-1H-indol-3-yl)-N,N-dimethylmethanamine (146886-51-3) → (S)-N-Benzyloxycarbonyl-4-(N-tert-butyloxycarbonyl)aminotryptophan methyl ester (252289-08-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: tBuLi / diethyl ether / 1.75 h / -78 - 0 °C

1.2: 73 percent / diethyl ether / 1 h / -78 °C

2.1: 91.7 percent / tetrahydrofuran / 20 °C

3.1: MeI / dimethylformamide / 20 °C

4.1: 6.51 g / TBAF / tetrahydrofuran / 1 h / 20 °C

5.1: morpholine / Pd[PPh₃]4 / tetrahydrofuran / 0.5 h / 20 °C

6.1: 3.42 g / dioxane / 0.5 h / Heating

7.1: 39 percent / aq. NaOH; penicillin G acylase / aq. methanol / 37 °C / pH 7.6

8.1: dioxane; aq. NaOH / 1 h / 20 °C

9.1: 0.903 g / methanol; CH₂Cl₂ / 0.5 h / 20 °C

With morpholine; sodium hydroxide; penicillin G acylase; tetrabutyl ammonium fluoride; tert.-butyl lithium; methyl iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; sodium hydroxide; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 4.1: Mannich-type reaction;

DOI:10.1002/1521-3765(20001103)6:21<3943::AID-CHEM3943<3.3.CO;2-K

Reference yield:

3-Dimethylaminomethyl-4-amino-1-triisopropylsilylindole (146886-61-5) → (S)-N-Benzyloxycarbonyl-4-(N-tert-butyloxycarbonyl)aminotryptophan methyl ester (252289-08-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 91.7 percent / tetrahydrofuran / 20 °C

2: MeI / dimethylformamide / 20 °C

3: 6.51 g / TBAF / tetrahydrofuran / 1 h / 20 °C

4: morpholine / Pd[PPh₃]4 / tetrahydrofuran / 0.5 h / 20 °C

5: 3.42 g / dioxane / 0.5 h / Heating

6: 39 percent / aq. NaOH; penicillin G acylase / aq. methanol / 37 °C / pH 7.6

7: dioxane; aq. NaOH / 1 h / 20 °C

8: 0.903 g / methanol; CH₂Cl₂ / 0.5 h / 20 °C

With morpholine; sodium hydroxide; penicillin G acylase; tetrabutyl ammonium fluoride; methyl iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; sodium hydroxide; dichloromethane; N,N-dimethyl-formamide; 3: Mannich-type reaction;

DOI:10.1002/1521-3765(20001103)6:21<3943::AID-CHEM3943<3.3.CO;2-K

Reference yield:

3-Dimethylaminomethyl-4-(N-tert-butyloxycarbonyl)amino-1-triisopropylsilylindole (252288-55-4) → (S)-N-Benzyloxycarbonyl-4-(N-tert-butyloxycarbonyl)aminotryptophan methyl ester (252289-08-0)

Guidance literature:

Multi-step reaction with 7 steps

1: MeI / dimethylformamide / 20 °C

2: 6.51 g / TBAF / tetrahydrofuran / 1 h / 20 °C

3: morpholine / Pd[PPh₃]4 / tetrahydrofuran / 0.5 h / 20 °C

4: 3.42 g / dioxane / 0.5 h / Heating

5: 39 percent / aq. NaOH; penicillin G acylase / aq. methanol / 37 °C / pH 7.6

6: dioxane; aq. NaOH / 1 h / 20 °C

7: 0.903 g / methanol; CH₂Cl₂ / 0.5 h / 20 °C

With morpholine; sodium hydroxide; penicillin G acylase; tetrabutyl ammonium fluoride; methyl iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; sodium hydroxide; dichloromethane; N,N-dimethyl-formamide; 2: Mannich-type reaction;

DOI:10.1002/1521-3765(20001103)6:21<3943::AID-CHEM3943<3.3.CO;2-K

upstream raw materials:

diazomethane

2-benzyloxycarbonylamino-3-(4-tert-butoxycarbonylamino-1H-indol-3-yl)-propionic acid

3-(Dimethylaminomethyl)indole

1-(N-triisopropylsilyl-1H-indol-3-yl)-N,N-dimethylmethanamine

Downstream raw materials:

(S)-(2-(4-amino-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester

(S,S)-(2-(4-((1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester

(-)-N¹³-Desmethyl-C¹²-desisopropyl-C¹²-phenylmethylindolactam V

Phenylmethyl (S,S)-2-{4-[1-(phenylmethyloxycarbonyl)ethylamino]-1H-indol-3-yl}-1-(hydroxymethyl)ethylcarbamate

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