Boc-l-alanine

Base Information

• Chemical Name: Boc-l-alanine
• CAS No.: 15761-38-3
• Deprecated CAS: 186665-28-1,207305-56-4,90580-61-3,911484-43-0
• Molecular Formula: C8H15NO4
• Molecular Weight: 189.211
• Hs Code.: 2924 19 00
• European Community (EC) Number: 239-847-8
• UNII: VBSZA1BT4G
• DSSTox Substance ID: DTXSID40884846
• Nikkaji Number: J208.111C
• Wikidata: Q72509662
• Mol file: 15761-38-3.mol

Synonyms:Boc-Ala;t-BA amino acid;tert-butoxycarbonyl-alanine;tert-butoxycarbonylalanine

Chemical Property of Boc-l-alanine

Chemical Property:

• Appearance/Colour: White to off-white microcrystalline powder
• Vapor Pressure: 6.39E-05mmHg at 25°C
• Melting Point: 79-83 °C(lit.)
• Refractive Index: -25.5 ° (C=2, AcOH)
• Boiling Point: 320.9 °C at 760 mmHg
• PKA: 4.02±0.10(Predicted)
• Flash Point: 147.9 °C
• PSA: 75.63000
• Density: 1.126 g/cm³
• LogP: 1.37510
• Storage Temp.: −20°C
• Solubility.: DMSO, Methanol
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 189.10010796
• Heavy Atom Count: 13
• Complexity: 207

Purity/Quality:

99% ^*data from raw suppliers

N-tert-Boc-L-alanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)O)NC(=O)OC(C)(C)C
• Isomeric SMILES: C[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• Uses: Boc-Ala-OH can be used: In the preparation of N-propargylalanine, a key precursor to generate N-(3-aryl)propylated alanine residues.In the resolution of racemic mixture of 3,3′-bis(benzyloxy)-1,1′-binaphthalene-2,2′-diol.In the one-pot synthesis of hybrid tripeptidomimetics containing both amide and imide functionalities.

Technology Process of Boc-l-alanine

There total 137 articles about Boc-l-alanine 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: 100.0%

D-Alanine (338-69-2,25191-17-7,18875-37-1) + di-tert-butyl dicarbonate (24424-99-5) → Boc-(R)-Ala (3744-87-4,7764-95-6,15761-38-3)

Guidance literature:

D-Alanine; With sodium hydroxide; In water; at 0 ℃; for 0.166667h;

di-tert-butyl dicarbonate; In tetrahydrofuran; water; at 20 ℃;

Reference yield: 84.0%

L-alanin (56-41-7,25191-17-7,18875-37-1) + O-(tert-butyl) S-(pyridin-2-yl)carbonothioate (105678-24-8) → 2-Sulfanylpyridine (2637-34-5,73018-10-7) + L-N-Boc-Ala (15761-38-3)

Guidance literature:

With triethylamine; In water; N,N-dimethyl-formamide; for 16h; Ambient temperature;

DOI:10.1246/bcsj.58.3570

Reference yield: 75.0%

(R)-2-tertbutoxycarbonylamino-1-propanol (79069-13-9,127516-56-7,147252-84-4,106391-86-0) → Boc-(R)-Ala (3744-87-4,7764-95-6,15761-38-3)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 0 - 20 ℃; for 1h;

DOI:10.1016/S0040-4039(02)02433-4

upstream raw materials:

tert-Butyl 4-nitrophenyl carbonate

rac-Ala-OH

tert-butyl alcohol

C₁₁H₁₉NO₆

Downstream raw materials:

N-tert-butoxycarbonyl-DL-alanine (SR)-3-oxo-2-trityl-isoxazolidin-4-ylamide

N-tert-butoxycarbonyl-DL-alanine (RS)-3-oxo-2-trityl-isoxazolidin-4-ylamide

Boc-(R)-Ala

N-tert-butoxycarbonyl-L-alanine ethyl ester

Refernces

SYNTHESIS OF A GLYCOTRIPEPTIDE AND A GLYCOSOMATOSTATIN CONTAINING THE 3-O-(2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL)-L-SERINE RESIDUE

10.1016/S0008-6215(00)85248-9

A study detailing the synthesis of a glycotripeptide and a glycosomatostatin, both containing the 3-O-(2-acetamido-2-deoxy-D-glucopyranosyl)-L-serine residue. The research was conducted by a team from the Salk Institute for Biological Studies and the University of California, San Diego. The process involved solid-phase synthesis to create the sequences Gly-[P-D-GlcpNAc-(1→3)-Ser]-Ala-OH and /I-D-GlcpNAc-(1→3)-Ser-13-somatostatin. The synthesized glycopeptides were found to be homogeneous upon examination through thin-layer chromatography (t.l.c.) and liquid chromatography (l.c.), and they exhibited the correct amino acid composition and 2-amino-2-deoxy-D-glucose content. The structure of one of the glycopeptides was confirmed by mass spectrometry and nuclear magnetic resonance (n.m.r.) spectroscopy. The study was supported by grants from the National Institute of Arthritis, Metabolism, and Digestive Diseases, the National Heart Institute, and the William Randolph Hearst Foundation, among others.