5-Bromo-N-Fmoc-L-tryptophan

Base Information

• Chemical Name: 5-Bromo-N-Fmoc-L-tryptophan
• CAS No.: 460751-66-0
• Molecular Formula: C26H21BrN2O4
• Molecular Weight: 505.36
• Mol file: 460751-66-0.mol

Synonyms:5-Bromo-N-Fmoc-L-tryptophan

Chemical Property of 5-Bromo-N-Fmoc-L-tryptophan

Chemical Property:

• PSA: 91.42000
• LogP: 5.85570

Purity/Quality:

98.5% ^*data from raw suppliers

Fmoc-Trp(5-Br)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Bromo-N-Fmoc-L-tryptophan

There total 8 articles about 5-Bromo-N-Fmoc-L-tryptophan 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: 71.0%

5-bromo-L-tryptophan hydrochloride (139684-34-7) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (S)-N-(fluoren-9-ylmethoxycarbonyl)-5-bromo-tryptophan (460751-66-0,925939-82-8)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1002/bip.23112

Reference yield:

5-bromo-1H-indole (10075-50-0) → (S)-N-(fluoren-9-ylmethoxycarbonyl)-5-bromo-tryptophan (460751-66-0,925939-82-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: trichlorophosphate / 0.17 h / 0 °C

1.2: 2 h / 45 °C

2.1: n-butyllithium / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

2.2: 2 h / 20 °C

3.1: hydrogenchloride / water / 3 h / Reflux

4.1: acetic acid / methanol / 16 h / 0 - 20 °C

5.1: potassium carbonate; dihydrogen peroxide / dimethyl sulfoxide / 6 h / 20 °C

6.1: trifluoroacetic acid; chlorotriisopropylsilane / 42 h / 60 °C

7.1: water; hydrogenchloride / 18 h / Reflux

8.1: sodium carbonate / tetrahydrofuran; water / 2 h / 20 °C

With hydrogenchloride; n-butyllithium; chlorotriisopropylsilane; water; dihydrogen peroxide; sodium carbonate; potassium carbonate; acetic acid; trifluoroacetic acid; trichlorophosphate; In tetrahydrofuran; methanol; water; dimethyl sulfoxide;

DOI:10.1039/c4ob02107j

Reference yield:

C11H10BrNO → (S)-N-(fluoren-9-ylmethoxycarbonyl)-5-bromo-tryptophan (460751-66-0,925939-82-8)

Guidance literature:

Multi-step reaction with 6 steps

1: hydrogenchloride / water / 3 h / Reflux

2: acetic acid / methanol / 16 h / 0 - 20 °C

3: potassium carbonate; dihydrogen peroxide / dimethyl sulfoxide / 6 h / 20 °C

4: trifluoroacetic acid; chlorotriisopropylsilane / 42 h / 60 °C

5: water; hydrogenchloride / 18 h / Reflux

6: sodium carbonate / tetrahydrofuran; water / 2 h / 20 °C

With hydrogenchloride; chlorotriisopropylsilane; water; dihydrogen peroxide; sodium carbonate; potassium carbonate; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; water; dimethyl sulfoxide;

DOI:10.1039/c4ob02107j

upstream raw materials:

5-bromo-1H-indole-3-carboxaldehyde

5-bromo-L-tryptophan hydrochloride

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

5-bromo-1H-indole

Refernces

• 1、 Chen, Chou-Hsiung,Genapathy, Sivaneswary,Fischer, Peter M.,Chan, Weng C.. "A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues". . p. 9764 - 9768. Retrieved 2015/01/09.