N5-[(1,1-Dimethylethoxy)carbonyl]-N2-[(2-propen-1-yloxy)carbonyl]-L-ornithine

Base Information

• Chemical Name: N5-[(1,1-Dimethylethoxy)carbonyl]-N2-[(2-propen-1-yloxy)carbonyl]-L-ornithine
• CAS No.: 947401-26-5
• Molecular Formula: C₁₄H₂₄N₂O₆
• Molecular Weight: 316.354
• Mol file: 947401-26-5.mol

Synonyms:N5-[(1,1-Dimethylethoxy)carbonyl]-N2-[(2-propen-1-yloxy)carbonyl]-L-ornithine

Chemical Property of N5-[(1,1-Dimethylethoxy)carbonyl]-N2-[(2-propen-1-yloxy)carbonyl]-L-ornithine

Chemical Property:

• Boiling Point: 504.9±50.0 °C(Predicted)
• PSA: 113.96000
• Density: 1.153±0.06 g/cm3(Predicted)
• LogP: 2.43850

Purity/Quality:

97% ^*data from raw suppliers

Aloc-L-Orn(Boc)-OH*DCHA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N5-[(1,1-Dimethylethoxy)carbonyl]-N2-[(2-propen-1-yloxy)carbonyl]-L-ornithine

There total 3 articles about N5-[(1,1-Dimethylethoxy)carbonyl]-N2-[(2-propen-1-yloxy)carbonyl]-L-ornithine 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: 90.0%

Nδ-(tert-butoxycarbonyl)-L-ornithine (13650-49-2,184576-63-4) + Allyl chloroformate (2937-50-0) → Alloc-Orn(Boc)-OH (947401-26-5)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; water; for 1.5h;

DOI:10.1021/ol800654n

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → Alloc-Orn(Boc)-OH (947401-26-5)

Guidance literature:

Multi-step reaction with 2 steps

2: NaHCO₃ / H₂O; dioxane / 16 h / 0 °C

With sodium hydrogencarbonate; In 1,4-dioxane; water;

DOI:10.1021/jo00376a101

Reference yield:

L-ornithine hydrochloride (3184-13-2,36630-89-4) → Alloc-Orn(Boc)-OH (947401-26-5)

Guidance literature:

Multi-step reaction with 2 steps

2: NaHCO₃ / H₂O; dioxane / 16 h / 0 °C

With sodium hydrogencarbonate; In 1,4-dioxane; water;

DOI:10.1021/jo00376a101

upstream raw materials:

N^δ-(tert-butoxycarbonyl)-L-ornithine

Allyl chloroformate

di-tert-butyl dicarbonate

L-ornithine hydrochloride

Downstream raw materials:

C₅₃H₈₅N₉O₁₄

(S)-2-(2,4-Dimethoxy-benzylamino)-5-(4-{(1S,2R)-2-[(E)-2-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-vinyl]-cyclopentyl}-but-2-ynoylamino)-pentanoic acid methyl ester

(S)-2-(2,4-Dimethoxy-benzylamino)-5-((Z)-4-{(1S,2R)-2-[(E)-2-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-vinyl]-cyclopentyl}-but-2-enoylamino)-pentanoic acid methyl ester

C₄₉H₇₉N₉O₁₁

Refernces

• 1、 Demmer,Dijkgraaf,Schottelius,Wester,Kessler. "Introduction of functional groups into peptides via N-alkylation". supporting information; experimental part. p. 2015 - 2018. Retrieved 2009/04/18.