5-Azidonorvaline

Base Information

• Chemical Name: 5-Azidonorvaline
• CAS No.: 156463-09-1
• Molecular Formula: C₅H₁₀N₄O₂
• Molecular Weight: 158.16
• Hs Code.: 9999999999
• DSSTox Substance ID: DTXSID40935463
• Nikkaji Number: J590.808F
• Wikidata: Q82911518
• Mol file: 156463-09-1.mol

Synonyms:5-Azidonorvaline;156463-09-1;5-Azido-L-norvaline;(2S)-2-AMINO-5-AZIDOPENTANOIC ACID;(S)-2-Amino-5-azidopentanoic acid hydrochloride;DTXSID40935463;AKOS030212888;EN300-7729844;Delta-azido-L-ornithine hydrochloride,delta-azido-L-norvaline hydrochloride,(S)-2-amino-5-azidopentanoic acid hydrochloride

Chemical Property of 5-Azidonorvaline

Chemical Property:

• PSA: 113.07000
• LogP: 0.64186
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 158.08037557
• Heavy Atom Count: 11
• Complexity: 175

Purity/Quality:

97% ^*data from raw suppliers

H-L-Orn(N3)-OH*HCl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CC(C(=O)O)N)CN=[N+]=[N-]
• Isomeric SMILES: C(C[C@@H](C(=O)O)N)CN=[N+]=[N-]

Technology Process of 5-Azidonorvaline

There total 7 articles about 5-Azidonorvaline 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%

(S)-benzyl 5-azido-2-(tert-butoxycarbonylamino)pentanoate (1224702-11-7) → 2-amino-5-azidopentanoic acid (156463-09-1)

Guidance literature:

With boron tribromide; In dichloromethane; at -10 - 20 ℃; for 3h;

DOI:10.1055/S-0029-1218391

Reference yield:

Boc-Orn(Z)-OH (2480-93-5) → 2-amino-5-azidopentanoic acid (156463-09-1)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / ethyl acetate / 16 h / 2068.59 Torr

2: 382 mg / K₂CO₃; aq. CuSO₄; TfN₃ / CH₂Cl₂; methanol

With triflic azide; hydrogen; potassium carbonate; copper(II) sulfate; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;

DOI:10.1021/ja047629c

Reference yield:

N2-(tert-butoxycarbonyl)-L-ornithine (21887-64-9) → 2-amino-5-azidopentanoic acid (156463-09-1)

Guidance literature:

With triflic azide; potassium carbonate; copper(II) sulfate; In methanol; dichloromethane;

DOI:10.1021/ja047629c

upstream raw materials:

N₂-(tert-butoxycarbonyl)-L-ornithine

Boc-Orn(Z)-OH

(2R)-N-<(2S)-2-<amino>-5-chloropentan-1-oyl>bornane-10.2-sultam

5-azido-2S-{[(1,1-dimethylethoxy)carbonyl]amino}pentanoic acid

Downstream raw materials:

N^α-(9-fluorenylmethyloxycarbonyl)-azido-L-ornithine

Refernces

• 1、 Isaad, Alexandra Le Chevalier,Barbetti, Francesca,Rovero, Paolo,D'Ursi, Anna Maria,Chelli, Mario,Chorev, Michael,Papini, Anna Maria. "Nα-Fmoc-protected ω-azido- and ω-alkynyl-L- amino acids as building blocks for the synthesis of "clickable" peptides". experimental part. p. 5308 - 5314. Retrieved 2009/06/18.
• 2、 Oppolzer,Moretti,Zhou. "Asymmetric alkylations of a sultam-derived glycine equivalent: Practical preparation of enantiomerically pure α-amino acids". . p. 2363 - 2380. Retrieved 2007/10/02.