N-Bsmoc-L-asparagine

Base Information

• Chemical Name: N-Bsmoc-L-asparagine
• CAS No.: 197245-31-1
• Molecular Formula: C14H14 N2 O7 S
• Molecular Weight: 354.34
• DSSTox Substance ID: DTXSID60428827
• Nikkaji Number: J1.135.238C
• Wikidata: Q82241658
• Mol file: 197245-31-1.mol

Synonyms:N-Bsmoc-L-asparagine;197245-31-1;(2S)-4-amino-2-[(1,1-dioxo-1-benzothiophen-2-yl)methoxycarbonylamino]-4-oxobutanoic acid;(((1,1-Dioxidobenzo[b]thiophen-2-yl)methoxy)carbonyl)-L-asparagine;SCHEMBL21851555;DTXSID60428827;AKOS024348911

Chemical Property of N-Bsmoc-L-asparagine

Chemical Property:

• Vapor Pressure: 3.98E-24mmHg at 25°C
• Melting Point: 136°C
• Refractive Index: 1.629
• Boiling Point: 757.7°Cat760mmHg
• PKA: 3.65±0.10(Predicted)
• Flash Point: 412°C
• PSA: 165.72000
• Density: 1.553g/cm³
• LogP: 2.30450
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 354.05217196
• Heavy Atom Count: 24
• Complexity: 665

Purity/Quality:

98%Min ^*data from raw suppliers

N-BSMOC-L-ASPARAGINE 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(CC(=O)N)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C=C(S2(=O)=O)COC(=O)N[C@@H](CC(=O)N)C(=O)O

Technology Process of N-Bsmoc-L-asparagine

There total 6 articles about N-Bsmoc-L-asparagine 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: 90.4%

L-asparagine (70-47-3,28088-48-4,7006-34-0) + N-(benzothiophenesulfone-2-methyl)-N-succinimidyl carbonate (197244-91-0) → Bsmoc-Asn-OH (197245-31-1)

Guidance literature:

With sodium hydrogencarbonate; In acetone; Ambient temperature;

DOI:10.1021/jo982140l

Reference yield:

benzothiophen-2-yllithium (50779-55-0) → Bsmoc-Asn-OH (197245-31-1)

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: 90.4 percent / NaHCO₃ / acetone / Ambient temperature

With sodium perborate; sodium tetrahydroborate; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; acetic acid; acetone;

DOI:10.1021/jo982140l

Reference yield:

benzothiophene-2-methanol (17890-56-1) → Bsmoc-Asn-OH (197245-31-1)

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: 90.4 percent / NaHCO₃ / acetone / Ambient temperature

With sodium perborate; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; acetic acid; acetone;

DOI:10.1021/jo982140l

upstream raw materials:

L-asparagine

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

benzothiophen-2-yllithium

benzothiophene-2-methanol

Refernces