Benzyl 3-(2,5-dioxo-1,3-oxazolidin-4-yl)propanoate

Base Information

• Chemical Name: Benzyl 3-(2,5-dioxo-1,3-oxazolidin-4-yl)propanoate
• CAS No.: 3190-71-4
• Molecular Formula: C13H13 N O5
• Molecular Weight: 263.25
• Hs Code.: 2934999090
• Nikkaji Number: J809.838G
• Mol file: 3190-71-4.mol

Synonyms:Glu(OBzl)NCA;10289-08-4;Benzyl 3-(2,5-dioxo-1,3-oxazolidin-4-yl)propanoate;Benzyl(R)-2,5-Dioxooxazolidine-4-propanoate;Benzyl 3-(2,5-dioxooxazolidin-4-yl)propanoate;Glu-(OBZL)-NCA;MFCD11046651;MFCD18251408;SCHEMBL4415882;AKOS030627578;AS-31486;SY069040;SY225313;FT-0698229;Benzyl3-(2,5-dioxooxazolidin-4-yl)propanoate;Benzyl (S)-2,5-Dioxooxazolidine-4-propanoate

Chemical Property of Benzyl 3-(2,5-dioxo-1,3-oxazolidin-4-yl)propanoate

Chemical Property:

• Melting Point: 97-98℃
• Refractive Index: 1.54
• PKA: 9.03±0.40(Predicted)
• PSA: 81.70000
• Density: 1.293g/cm3
• LogP: 1.47380
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Acetonitrle (Slightly), Chloroform (Slightly), DMSO (Slightly), THF (Slightly)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 263.07937252
• Heavy Atom Count: 19
• Complexity: 362

Purity/Quality:

99.9% ^*data from raw suppliers

(4S)-2,5-Dioxo-4-oxazolidinepropanoicAcidPhenylmethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)CCC2C(=O)OC(=O)N2
• Uses: H-GLU(OBZL)-NCA was used in the synthesis and physicochemical characterization of reduction-sensitive block copolymer for intracellular delivery of doxoru bicin. (4S)-2,5-Dioxo-4-oxazolidinepropanoic Acid Phenylmethyl Ester was used in the synthesis and physicochemical characterization of reduction-sensitive block copolymer for intracellular delivery of doxorubicin.

Technology Process of Benzyl 3-(2,5-dioxo-1,3-oxazolidin-4-yl)propanoate

There total 24 articles about Benzyl 3-(2,5-dioxo-1,3-oxazolidin-4-yl)propanoate 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) + L-glutamic acid γ-benzyl ester (29456-09-5,25014-27-1) → 3-(2,5-dioxo-oxazolidin-4-yl)-propionic acid benzyl ester (5254-51-3,3190-71-4,10289-08-4,13822-45-2)

Guidance literature:

In tetrahydrofuran; at 50 ℃; for 1h;

DOI:10.1021/ol0622965

Reference yield: 95.4%

phosgene (75-44-5) + L-glutamic acid γ-benzyl ester (1676-73-9,25014-27-1) → 5-benzyl L-glutamate N-carboxyanhydride (3190-71-4)

Guidance literature:

In tetrahydrofuran; toluene; at 50 ℃; for 1h;

Reference yield: 95.1%

bis(trichloromethyl) carbonate (32315-10-9) + L-glutamic acid γ-benzyl ester (1676-73-9,25014-27-1) → 5-benzyl L-glutamate N-carboxyanhydride (3190-71-4)

Guidance literature:

In tetrahydrofuran; at 40 ℃; Inert atmosphere;

DOI:10.1039/c5ra20972b

upstream raw materials:

phosgene

L-glutamic acid γ-benzyl ester

N-benzyloxycarbonyl-5-O-benzyl-L-glutamic acid

Boc-Glu(OBzl)-OH

Downstream raw materials:

1,2-propylene cyclic carbonate

4-Phenyl-1,3-dioxolan-2-one

C₁₂₄H₁₄₁N₁₁O₃₀

L-Glutamohydroxamsaeure-γ-benzylester

Refernces

• 1、 Lv, Shixian,Kim, Hojun,Song, Ziyuan,Feng, Lin,Yang, Yingfeng,Baumgartner, Ryan,Tseng, Kuan-Ying,Dillon, Shen J.,Leal, Cecilia,Yin, Lichen,Cheng, Jianjun. "Unimolecular Polypeptide Micelles via Ultrafast Polymerization of N-Carboxyanhydrides". . p. 8570 - 8574. Retrieved 2020.
• 2、 Whitton, Greg,Gauthier, Mario. "Arborescent polypeptides from γ-benzyl l -glutamic acid". . p. 5270 - 5279. Retrieved 2013.
• 3、 Mazzier, Daniela,Maran, Marco,Polo Perucchin, Omar,Crisma, Marco,Zerbetto, Mirco,Causin, Valerio,Toniolo, Claudio,Moretto, Alessandro. "Photoresponsive supramolecular architectures based on polypeptide hybrids". . p. 7272 - 7283. Retrieved 2014.
• 4、 Tong, Fei,Tang, Xiangyuan,Li, Xin,Xia, Wenquan,Liu, Daojun. "The effect of insulin-loaded linear poly(Ethylene glycol)-brush-like poly(L-lysine) block copolymer on renal ischemia/reperfusion-induced lung injury through downregulating hypoxia-inducible factor". . p. 1717 - 1730. Retrieved 2016.
• 5、 Poche, Drew S.,Moore, Michael J.,Bowles, Jennifer L.. "An unconventional method for purifying the N-carboxyanhydride derivatives of γ-alkyl-L-glutamates". . p. 843 - 854. Retrieved 1999.
• 6、 Obeid, Rodolphe,Scholz, Carmen. "Synthesis and self-assembly of well-defined poly(amino acid) end-capped poly(ethylene glycol) and poly(2-methyl-2-oxazoline)". . p. 3797 - 3804. Retrieved 2011.
• 7、 Kim, Jonghyub,Park, Jaehyun,Lee, Seongyeol,Sohn, Daewon. "Surface-grafting of polyglutamate on Si wafer using micro contact printing". . p. 211 - 216. Retrieved 2007.
• 8、 Sedla?ík, Tomá?,Proks, Vladimír,?louf, Miroslav,Du?ková-Smr?ková, Miroslava,Studenovská, Hana,Rypá?ek, Franti?ek. "Macroporous Biodegradable Cryogels of Synthetic Poly(α-amino acids)". . p. 3455 - 3465. Retrieved 2015.
• 9、 Robson Marsden, Hana,Handgraaf, Jan-Willem,Nudelman, Fabio,Sommerdijk, Nico A.J.M.,Kros, Alexander. "Uniting polypeptides with sequence-designed peptides: Synthesis and assembly of poly(γ-benzyl L-glutamate)-b-coiled-coil peptide copolymers". . p. 2370 - 2377. Retrieved 2010.
• 10、 Holley, Andrew C.,Ray, Jacob G.,Wan, Wenming,Savin, Daniel A.,McCormick, Charles L.. "Endolytic, pH-responsive HPMA-b-(l-Glu) copolymers synthesized via sequential aqueous RAFT and ring-opening polymerizations". . p. 3793 - 3799. Retrieved 2013.