Fmoc-Trp(Boc)-OH

Base Information

• Chemical Name: Fmoc-Trp(Boc)-OH
• CAS No.: 143824-78-6
• Molecular Formula: C31H30N2O6
• Molecular Weight: 526.589
• Hs Code.: 29339900
• UNII: X3V4CFM5R8
• DSSTox Substance ID: DTXSID60431755
• Nikkaji Number: J956.294J
• Wikidata: Q72479067
• Mol file: 143824-78-6.mol

Synonyms:Fmoc-Trp(Boc)-OH;143824-78-6;Fmoc-L-Trp(Boc)-OH;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-3-yl]propanoic acid;Na-(((9H-fluoren-9-yl)methoxy)carbonyl)-1-(tert-butoxycarbonyl)-L-tryptophan;1-[(1,1-Dimethylethoxy)carbonyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-tryptophan;L-Tryptophan, 1-[(1,1-dimethylethoxy)carbonyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)propanoic acid;3-[(2S)-2-Carboxy-2-[[[(9H-fluoren-9-yl)methoxy]carbonyl]amino]ethyl]indole-1-carboxylic acid tert-butyl ester;MFCD00153366;Nalpha-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N1-tert-butoxycarbonyl-L-tryptophan;FMOC-NIN-T-BUTYLOXYCARBONYL-L-TRYPTOPHAN;X3V4CFM5R8;SCHEMBL1709188;DTXSID60431755;N1-Boc-Nalpha-Fmoc-L-tryptophan;ADOHASQZJSJZBT-SANMLTNESA-N;AMY22591;N-|A-Fmoc-N(in)-Boc-L-tryptophan;AKOS015924241;CS-W008034;HY-W008034;AS-12079;F0507;Fmoc-Trp(Boc)-OH, >=97.0% (HPLC);A26742;EN300-249916;M03376;Q-101761;N-tert-Butoxycarbonyl-N-9-fluorenylmethoxycarbonyl-L-tryptophan;N-alpha-(9-Fluorenylmethyloxycarbonyl)-N1-tert-butyloxycarbonyl-L-tryptophan;(2S)-3-{1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)propanoic acid

Chemical Property of Fmoc-Trp(Boc)-OH

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Melting Point: 86 - 90 °C
• Refractive Index: -20 ° (C=1, DMF)
• PKA: 3.71±0.10(Predicted)
• PSA: 106.86000
• Density: 1.289 g/cm³
• LogP: 6.34980
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• XLogP3: 6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 526.21038668
• Heavy Atom Count: 39
• Complexity: 880

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N
• Statements: 36/37/38-51/53-43
• Safety Statements: 22-24/25-36/37/39-27-26-61-37-24

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C=C(C2=CC=CC=C21)CC(C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35
• Isomeric SMILES: CC(C)(C)OC(=O)N1C=C(C2=CC=CC=C21)C[C@@H](C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35
• Uses: Fmoc-Trp(Boc)-OH is a very useful synthetic intermediate. It is used to prepare Trp containing-peptides. Fmoc-Trp(Boc)-OH can be used for the synthesis of analogs of glucagon-like peptide-1 (GLP-1) for the treatment of type 2 diabetes and various peptides by Fmoc solid phase peptide synthesis (SPPS).

Technology Process of Fmoc-Trp(Boc)-OH

There total 10 articles about Fmoc-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.