Boc-δ-azido-Nva-OH · DCHA

Base Information

• Chemical Name: Boc-δ-azido-Nva-OH · DCHA
• CAS No.: 763139-35-1
• Molecular Formula: C10H18N4O4
• Molecular Weight: 258.27400
• Mol file: 763139-35-1.mol

Synonyms:5-azido-2S-{[(1,1-dimethylethoxy)carbonyl]amino}pentanoic acid;Nα-tert-butoxycarbonyl δ-azido-L-norvaline;5-azido-2-((tert-butoxycarbonyl)amino)pentanoic acid;N-alpha-t-Butyloxycarbonyl-δ-azido-L-ornithine, N-alpha-t-Butyloxycarbonyl-delta-azido-L-norvaline, (S)-2-t-Butyloxycarbonylamino-5-azidopentanoic acid;Boc-Orn(N3)-OH;Nα-tert-butoxycarbonyl Nε-azido-L-norvaline;Nα-Boc-L-Nva(δ-N3)-OH;

Chemical Property of Boc-δ-azido-Nva-OH · DCHA

Chemical Property:

• PSA: 125.38000
• LogP: 1.89846

Purity/Quality:

98.5% ^*data from raw suppliers

Boc-L-Orn(N3)-OH*CHA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Boc-δ-azido-Nva-OH · DCHA

There total 3 articles about Boc-δ-azido-Nva-OH · DCHA 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: 61.0%

N2-(tert-butoxycarbonyl)-L-ornithine (21887-64-9) → 5-azido-2S-{[(1,1-dimethylethoxy)carbonyl]amino}pentanoic acid (763139-35-1)

Guidance literature:

With imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; potassium carbonate; In methanol; at 20 ℃; for 17h;

DOI:10.1021/jo101670a

Reference yield:

Boc-Orn(Z)-OH (2480-93-5) → 5-azido-2S-{[(1,1-dimethylethoxy)carbonyl]amino}pentanoic acid (763139-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 22 h / 20 °C

2: imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; potassium carbonate / methanol / 17 h / 20 °C

With imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; palladium 10% on activated carbon; hydrogen; potassium carbonate; In methanol;

DOI:10.1021/jo101670a

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-amino-5-azidopentanoic acid hydrochloride → 5-azido-2S-{[(1,1-dimethylethoxy)carbonyl]amino}pentanoic acid (763139-35-1)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 0 - 20 ℃;

DOI:10.1002/jlcr.3297

upstream raw materials:

N₂-(tert-butoxycarbonyl)-L-ornithine

Boc-Orn(Z)-OH

di-tert-butyl dicarbonate

Downstream raw materials:

(S)-benzyl 5-azido-2-(tert-butoxycarbonylamino)pentanoate

2-amino-5-azidopentanoic acid

Refernces

• 1、 Isidro-Llobet, Albert,Hadje Georgiou, Kathy,Galloway, Warren R. J. D.,Giacomini, Elisa,Hansen, Mette R.,Méndez-Abt, Gabriela,Tan, Yaw Sing,Carro, Laura,Sore, Hannah F.,Spring, David R.. "A diversity-oriented synthesis strategy enabling the combinatorial-type variation of macrocyclic peptidomimetic scaffolds". supporting information. p. 4570 - 4580. Retrieved 2015/04/14.
• 2、 Yu, Jingxian,Horsley, John R.,Moore, Katherine E.,Shapter, Joe G.,Abell, Andrew D.. "The effect of a macrocyclic constraint on electron transfer in helical peptides: A step towards tunable molecular wires". supporting information. p. 1652 - 1654. Retrieved 2014/02/14.