Fmoc-D-Trp(Boc)-OH

Base Information

• Chemical Name: Fmoc-D-Trp(Boc)-OH
• CAS No.: 163619-04-3
• Molecular Formula: C₃₁H₃₀N₂O₆
• Molecular Weight: 526.589
• Hs Code.: 29339900
• Mol file: 163619-04-3.mol

Synonyms:N-α-Fmoc-N-in-Boc-D-tryptophan;N-alpha-Fmoc-N(in)-Boc-D-tryptophan;N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-in-tert-butyl-oxycarbonyl-D-tryptophan;

Chemical Property of Fmoc-D-Trp(Boc)-OH

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Melting Point: 86 - 92oC (Decomposes)
• Refractive Index: 1.632
• PKA: 3.71±0.10(Predicted)
• PSA: 106.86000
• Density: 1.289 g/cm³
• LogP: 6.34980
• Storage Temp.: 2-8°C

Purity/Quality:

≥98%,≥99%, ^*data from raw suppliers

Fmoc-D-Trp(Boc)-OH ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Fmoc-D-Trp(Boc)-OH, is an amino acid derivative used in peptide chemistry.

Technology Process of Fmoc-D-Trp(Boc)-OH

There total 10 articles about Fmoc-D-Trp(Boc)-OH 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: 80.7%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (2S)-2-amino-3-(1-tert-butoxycarbonylindol-3-yl)propanoic acid (146645-63-8) → 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6,163619-04-3)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; Reagent/catalyst; Solvent;

Reference yield:

(S)-tert-butyl 2-(hydroxyamino)propanoate (83451-16-5,57001-44-2) + C37H37N3O5S (1019691-72-5) → Fmoc-Trp(Boc)-Ala-OtBu (1019691-19-0) + 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6,163619-04-3)

Guidance literature:

C₃₇H₃₇N₃O₅S; With Oxone; In water; N,N-dimethyl-formamide; at 25 ℃;

(S)-tert-butyl 2-(hydroxyamino)propanoate; In N,N-dimethyl-formamide; at 40 ℃; Further stages.;

DOI:10.1021/ja800053t

Reference yield:

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6,163619-04-3)

Guidance literature:

Multi-step reaction with 5 steps

1: thionyl chloride / -10 °C / Reflux

2: pyridine / tetrahydrofuran / -10 - 20 °C

3: 4-pyrrolidin-1-ylpyridine / acetonitrile / 20 °C

4: potassium carbonate; water / methanol / 20 °C

5: sodium hydrogencarbonate / tetrahydrofuran; water / 20 °C

With pyridine; thionyl chloride; water; sodium hydrogencarbonate; potassium carbonate; 4-pyrrolidin-1-ylpyridine; In tetrahydrofuran; methanol; water; acetonitrile;

upstream raw materials:

(S)-tert-butyl 2-(hydroxyamino)propanoate

C₃₇H₃₇N₃O₅S

methyl (2S)-3-(1H-indol-3-yl)-2-(trifluoroacetamido)propanoate

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

Refernces

• 1、 -. "Method for preparing pharmaceutical intermediate of tryptophan derivative". . . Retrieved 2021/09/21.
• 2、 Ju, Lei,Lippert, Alexander R.,Bode, Jeffrey W.. "Stereoretentive synthesis and chemoselective amide-forming ligations of C-terminal peptide α-ketoacids". . p. 4253 - 4255. Retrieved 2008/12/20.