N-Bsmoc-L-phenylalanine

Base Information

• Chemical Name: N-Bsmoc-L-phenylalanine
• CAS No.: 197245-19-5
• Molecular Formula: C19H17 N O6 S
• Molecular Weight: 387.41
• DSSTox Substance ID: DTXSID50428831
• Nikkaji Number: J1.135.226J
• Wikidata: Q82241663
• Mol file: 197245-19-5.mol

Synonyms:N-Bsmoc-L-phenylalanine;197245-19-5;(2S)-2-[(1,1-dioxo-1-benzothiophen-2-yl)methoxycarbonylamino]-3-phenylpropanoic acid;(((1,1-Dioxidobenzo[b]thiophen-2-yl)methoxy)carbonyl)-L-phenylalanine;L-Phenylalanine, N-[[(1,1-dioxidobenzo[b]thien-2-yl)methoxy]carbonyl]-;DTXSID50428831;N-(Benzo[b]thiophenesulfone-2-methoxycarbonyl)-L-phenylalanine;AKOS024286926;N-[(1-Benzothiophene 1,1-dioxide)-2-ylmethoxycarbonyl]-L-phenylalanine

Chemical Property of N-Bsmoc-L-phenylalanine

Chemical Property:

• Vapor Pressure: 6.83E-19mmHg at 25°C
• Melting Point: 167-169°C
• Refractive Index: 1.637
• Boiling Point: 670.5°Cat760mmHg
• Flash Point: 359.3°C
• Density: 1.427g/cm³
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 387.07765844
• Heavy Atom Count: 27
• Complexity: 690

Purity/Quality:

99% ^*data from raw suppliers

N-BSMOC-L-PHENYLALANINE 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)NC(=O)OCC2=CC3=CC=CC=C3S2(=O)=O
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)OCC2=CC3=CC=CC=C3S2(=O)=O

Technology Process of N-Bsmoc-L-phenylalanine

There total 5 articles about N-Bsmoc-L-phenylalanine 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:

benzothiophen-2-yllithium (50779-55-0) → Bsmoc-Phe-OH (197245-19-5)

Guidance literature:

Multi-step reaction with 4 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: 1.) Me₃SiCl, 2.) i-Pr₂NEt / 1.) CH₂Cl₂, reflux, 1 h, 2.) 0 deg C 20 min,; room temperature, 1-1.5 h

With sodium perborate; sodium tetrahydroborate; chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; acetic acid;

DOI:10.1021/jo982140l

Reference yield:

benzothiophene-2-methanol (17890-56-1) → Bsmoc-Phe-OH (197245-19-5)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 1.) Me₃SiCl, 2.) i-Pr₂NEt / 1.) CH₂Cl₂, reflux, 1 h, 2.) 0 deg C 20 min,; room temperature, 1-1.5 h

With sodium perborate; chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; acetic acid;

DOI:10.1021/jo982140l

Reference yield:

1,1-dioxobenzo[b]thiophen-2-ylmethanol (134996-50-2) → Bsmoc-Phe-OH (197245-19-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 36.1 g / tetrahydrofuran / -30 - 20 °C

2: 1.) Me₃SiCl, 2.) i-Pr₂NEt / 1.) CH₂Cl₂, reflux, 1 h, 2.) 0 deg C 20 min,; room temperature, 1-1.5 h

With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1021/jo982140l

upstream raw materials:

L-phenylalanine

1,1-dioxobenzo[b]thiophen-2-ylmethyl chloroformate

benzothiophen-2-yllithium

benzothiophene-2-methanol

Downstream raw materials:

Bsmoc-Phe-ψ(NH-CO-NH)-Val-OEt

Bsmoc-Phe-F

Refernces