N6-Carbobenzoxy-L-lysine N-Carboxyanhydride

Base Information

• Chemical Name: N6-Carbobenzoxy-L-lysine N-Carboxyanhydride
• CAS No.: 1676-86-4
• Molecular Formula: C₁₅H₁₈N₂O₅
• Molecular Weight: 306.318
• DSSTox Substance ID: DTXSID20433230
• Nikkaji Number: J721.945H
• Wikidata: Q82247359
• Mol file: 1676-86-4.mol

Synonyms:1676-86-4;N6-Carbobenzoxy-L-lysine N-Carboxyanhydride;(S)-Benzyl (4-(2,5-dioxooxazolidin-4-yl)butyl)carbamate;benzyl N-[4-[(4S)-2,5-dioxo-1,3-oxazolidin-4-yl]butyl]carbamate;(S)-4-[4-(Cbz-amino)butyl]oxazolidine-2,5-dione;MFCD16036317;BENZYL N-{4-[(4S)-2,5-DIOXO-1,3-OXAZOLIDIN-4-YL]BUTYL}CARBAMATE;SCHEMBL7252817;DTXSID20433230;AKOS027322593;N-[(4S)-4-(2,5-Dioxo-4-oxazolidinyl)butyl]carbamic Acid Phenylmethyl Ester;HY-W092115;s11720;BS-16191;CS-0137983;(S)-Benzyl(4-(2,5-dioxooxazolidin-4-yl)butyl)carbamate;Benzyl {4-[(4S)-2,5-dioxo-1,3-oxazolidin-4-yl]butyl}carbamate;Carbamic acid, [4-(2,5-dioxo-4-oxazolidinyl)butyl]-, phenylmethyl ester,(S)-

Chemical Property of N6-Carbobenzoxy-L-lysine N-Carboxyanhydride

Chemical Property:

• PKA: 9.31±0.40(Predicted)
• PSA: 100.71000
• Density: 1.248 g/cm³
• LogP: 1.56250
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Very Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 306.12157168
• Heavy Atom Count: 22
• Complexity: 407

Purity/Quality:

98%,99%, ^*data from raw suppliers

N6-Carbobenzoxy-L-lysine N-carboxyanhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NCCCCC2C(=O)OC(=O)N2
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)NCCCC[C@H]2C(=O)OC(=O)N2
• Uses: Like a L-lysine derivative, N6-Carbobenzoxy-L-lysine N-Carboxyanhydride can be used in the preparation of Polylysine, a synthetic, basic poly-α-amino acid. A L-lysine derivative used in the preparation of Polylysine, a synthetic, basic poly-α-amino acid. Polylysine inhibited fungal penetration and polyphenol formation in susceptible sweet potatoes infected with C. fimbriata and caused some inhibition of fungal growth, a lessening of the penetration by the fungus, and more callus formation in resistant sweet potatoes. The compound inhibited the infection of tomato cuttings by F. lycopersici but was also toxic to the plants. Polyglutamic acid had no effect on the fungi in vitro.

Technology Process of N6-Carbobenzoxy-L-lysine N-Carboxyanhydride

There total 20 articles about N6-Carbobenzoxy-L-lysine N-Carboxyanhydride 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%

bis(trichloromethyl) carbonate (32315-10-9) + N6-[(benzyloxy)carbonyl]-L-lysine (1155-64-2,57705-97-2,67178-46-5,25931-47-9) → N-benzyloxycarbonyl-L-lysine N-carboxyanhydride (1676-86-4,10289-12-0,47234-64-0,68199-92-8)

Guidance literature:

In tetrahydrofuran; for 12h;

Reference yield: 99.0%

N,N'-di-[(phenylmethoxy)carbonyl]-L-lysine (405-39-0) → N-benzyloxycarbonyl-L-lysine N-carboxyanhydride (1676-86-4,10289-12-0,47234-64-0,68199-92-8)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 10 ℃; for 3h;

Reference yield: 95.7%

1,1,1,3,3,3-hexachloro-propan-2-one (116-16-5) + N6-[(benzyloxy)carbonyl]-L-lysine (1155-64-2,57705-97-2,67178-46-5,25931-47-9) → N-benzyloxycarbonyl-L-lysine N-carboxyanhydride (1676-86-4,10289-12-0,47234-64-0,68199-92-8)

Guidance literature:

In tetrahydrofuran; at 50 ℃; Inert atmosphere;

DOI:10.1039/c0jm03385e

upstream raw materials:

N,N'-di-[(phenylmethoxy)carbonyl]-L-lysine

N₆-[(benzyloxy)carbonyl]-L-lysine

phosgene

trichloromethyl chloroformate

Downstream raw materials:

tetra-(N-carbobenzoxy-L-lysine)

Refernces

• 1、 Soria-Carrera, Héctor,Franco-Castillo, Isabel,Romero, Pilar,Martín, Santiago,de la Fuente, Jesús M.,Mitchell, Scott G.,Martín-Rapún, Rafael. "On-POM Ring-Opening Polymerisation of N-Carboxyanhydrides". supporting information. p. 3449 - 3453. Retrieved 2021/02/05.
• 2、 Long, Mengmeng,Liu, Xuemeng,Huang, Xu,Lu, Min,Wu, Xiaomei,Weng, Lingyan,Chen, Qiuping,Wang, Xueting,Zhu, Li,Chen, Zhongping. "Alendronate-functionalized hypoxia-responsive polymeric micelles for targeted therapy of bone metastatic prostate cancer". . p. 303 - 317. Retrieved 2021/05/06.