Fmoc-4-methyl-DL-tryptophan

Base Information

• Chemical Name: Fmoc-4-methyl-DL-tryptophan
• CAS No.: 1219279-39-6
• Molecular Formula: C₂₇H₂₄N₂O₄
• Molecular Weight: 440.499
• Mol file: 1219279-39-6.mol

Synonyms:Fmoc-4-methyl-DL-tryptophan;N-Fmoc-4-methyl-DL-tryptophan

Chemical Property of Fmoc-4-methyl-DL-tryptophan

Chemical Property:

Purity/Quality:

98%Min ^*data from raw suppliers

N-Fmoc-4-methyl-DL-tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: N-Fmoc-4-methyl-DL-tryptophan is used as a reactant in the preparation of p53 peptidomimetic macrocycles.

Technology Process of Fmoc-4-methyl-DL-tryptophan

There total 6 articles about Fmoc-4-methyl-DL-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: 68.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + D-Trp(4-Me)-OH trifluoroacetate → Fmoc-D-Trp(4-Me) (1219279-39-6)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; at 20 - 27 ℃; for 18h;

Reference yield:

C22H30N2O6 → Fmoc-D-Trp(4-Me) (1219279-39-6)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane / 1 h

2: sodium hydrogencarbonate / water; acetone / 18 h / 20 - 27 °C

With sodium hydrogencarbonate; In dichloromethane; water; acetone;

Reference yield:

tert-butyl 4-methyl-1H-indole-1-carboxylate (136540-84-6) → Fmoc-D-Trp(4-Me) (1219279-39-6)

Guidance literature:

Multi-step reaction with 5 steps

1: N-Bromosuccinimide / tetrahydrofuran / 18 h / 20 - 27 °C

2: iodine; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; zinc / N,N-dimethyl-formamide / 50 °C / Inert atmosphere

3: lithium hydroxide monohydrate / methanol; water / 3 h / 20 - 27 °C

4: dichloromethane / 1 h

5: sodium hydrogencarbonate / water; acetone / 18 h / 20 - 27 °C

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; N-Bromosuccinimide; lithium hydroxide monohydrate; iodine; sodium hydrogencarbonate; zinc; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

upstream raw materials:

tert-butyl 4-methyl-1H-indole-1-carboxylate

N-Boc-3-bromo-4-methylindole

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

4-methyl-1H-indole

Refernces