N-Bsmoc-L-tryptophan

Base Information

• Chemical Name: N-Bsmoc-L-tryptophan
• CAS No.: 197245-27-5
• Molecular Formula: C₂₁H₁₈N₂O₆S
• Molecular Weight: 426.45
• DSSTox Substance ID: DTXSID10428832
• Nikkaji Number: J1.135.234K
• Wikidata: Q82241664
• Mol file: 197245-27-5.mol

Synonyms:N-Bsmoc-L-tryptophan;197245-27-5;(2S)-2-[(1,1-dioxo-1-benzothiophen-2-yl)methoxycarbonylamino]-3-(1H-indol-3-yl)propanoic acid;DTXSID10428832;AKOS024348919

Chemical Property of N-Bsmoc-L-tryptophan

Chemical Property:

• Vapor Pressure: 7.52E-25mmHg at 25°C
• Melting Point: 80-106℃
• Refractive Index: 1.693
• Boiling Point: 768.6°Cat760mmHg
• PKA: 3.86±0.10(Predicted)
• Flash Point: 418.7°C
• PSA: 133.94000
• Density: 1.501g/cm³
• LogP: 4.18990
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 426.08855747
• Heavy Atom Count: 30
• Complexity: 805

Purity/Quality:

98%Min ^*data from raw suppliers

BSMOC-TRP-OH 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(S2(=O)=O)COC(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C=C(S2(=O)=O)COC(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)O

Technology Process of N-Bsmoc-L-tryptophan

There total 6 articles about N-Bsmoc-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: 92.0%

N-(benzothiophenesulfone-2-methyl)-N-succinimidyl carbonate (197244-91-0) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → Bsmoc-Trp-OH (197245-27-5)

Guidance literature:

With triethylamine; In water; acetonitrile; for 0.75h; Ambient temperature; pH 8.5-9;

DOI:10.1021/jo982140l

Reference yield:

benzothiophen-2-yllithium (50779-55-0) → Bsmoc-Trp-OH (197245-27-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 2.) NaBH₄ / 2.) MeOH

2: 75 percent / sodium perborate tetrahydrate / acetic acid / 45 - 50 °C

3: 36.1 g / tetrahydrofuran / -30 - 20 °C

4: 74 percent / CH₂Cl₂ / 20 h

5: 92 percent / Et₃N / acetonitrile; H₂O / 0.75 h / Ambient temperature; pH 8.5-9

With sodium perborate; sodium tetrahydroborate; triethylamine; In tetrahydrofuran; dichloromethane; water; acetic acid; acetonitrile;

DOI:10.1021/jo982140l

Reference yield:

benzothiophene-2-methanol (17890-56-1) → Bsmoc-Trp-OH (197245-27-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / sodium perborate tetrahydrate / acetic acid / 45 - 50 °C

2: 36.1 g / tetrahydrofuran / -30 - 20 °C

3: 74 percent / CH₂Cl₂ / 20 h

4: 92 percent / Et₃N / acetonitrile; H₂O / 0.75 h / Ambient temperature; pH 8.5-9

With sodium perborate; triethylamine; In tetrahydrofuran; dichloromethane; water; acetic acid; acetonitrile;

DOI:10.1021/jo982140l

upstream raw materials:

N-(benzothiophenesulfone-2-methyl)-N-succinimidyl carbonate

L-Tryptophan

benzothiophen-2-yllithium

benzothiophene-2-methanol

Refernces