(S)-(-)-4-BENZYLOXAZOLIDINE-2,5-DIONE

Base Information

• Chemical Name: (S)-(-)-4-BENZYLOXAZOLIDINE-2,5-DIONE
• CAS No.: 14825-82-2
• Molecular Formula: C10H9NO3
• Molecular Weight: 191.186
• Hs Code.: 2934999090
• Mol file: 14825-82-2.mol

Synonyms:2,5-Oxazolidinedione,4-(phenylmethyl)-, (S)-;2,5-Oxazolidinedione, 4-benzyl-, L- (8CI);(-)-4-Benzyl-2,5-oxazolidinedione;(S)-4-(Phenylmethyl)-2,5-oxazolidinedione;L-Phenylalanine N-carboxy anhydride;N-Carboxy-L-phenylalanine anhydride;N-Carboxy-L-phenylalanine cyclic anhydride;Phenylalanine N-carboxy anhydride;Phenylalanine-N-carboxy acid anhydride;(4S)-4-Benzyl-1,3-oxazolidine-2,5-dione;

Chemical Property of (S)-(-)-4-BENZYLOXAZOLIDINE-2,5-DIONE

Chemical Property:

• Melting Point: 90 °C
• Refractive Index: 1.569
• PKA: 9.32±0.40(Predicted)
• PSA: 55.40000
• Density: 1.3 g/cm³
• LogP: 1.19290
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

98%min ^*data from raw suppliers

(S)-4-Benzyloxazolidine-2,5-dione ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (S)-4-Benzyloxazolidine-2,5-dione, can be used in the synthesis of amphiphilic anionic copolymer, methoxy poly(ethylene glycol)-b-poly(l-glutamic acid-co-l-phenylalanine) (mPEG-b-P(Glu-co-Phe)), used as an efficient drug delivery system for an anticancer drug doxorubicin hydrochloride (DOX·HCl).

Technology Process of (S)-(-)-4-BENZYLOXAZOLIDINE-2,5-DIONE

There total 20 articles about (S)-(-)-4-BENZYLOXAZOLIDINE-2,5-DIONE 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-phenylalanine sodium salt (16480-57-2) → L-phenylalanine-N-carboxyanhydride (14825-82-2)

Guidance literature:

With 4-methyl-morpholine; In water; acetonitrile; at 20 ℃; for 0.00277778h; Reagent/catalyst; Flow reactor; Inert atmosphere;

DOI:10.1002/anie.201803549

Reference yield: 100.0%

oxalyl dichloride (79-37-8) + C20H33NO4Si (130529-77-0) → L-phenylalanine-N-carboxyanhydride (14825-82-2)

Guidance literature:

With N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo00212a042

Reference yield: 98.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → L-phenylalanine-N-carboxyanhydride (14825-82-2)

Guidance literature:

With phosphorus trichloride; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(01)85371-0

upstream raw materials:

phosgene

L-phenylalanine

oxalyl dichloride

C₂₀H₃₃NO₄Si

Downstream raw materials:

L-Phenylalanin-N-hydroxy-glycin

(S,S)-N,N'-bis(1-carboxy-2-phenylethyl)urea

(S)-4-benzyl-3-(2-nitro-phenylsulfanyl)-oxazolidine-2,5-dione

(S)-4-Benzyl-2,5-dioxo-oxazolidine-3-carboxylic acid 9H-fluoren-9-ylmethyl ester

Refernces

• 1、 Lee, Hyunpyo,Park, Jun Beum,Chang, Ji Young. "Synthesis of poly(ethylene glycol)/polypeptide/poly(D, L -lactide) copolymers and their nanoparticles". . p. 2859 - 2865. Retrieved 2011.
• 2、 Waku, Tomonori,Matsumoto, Masahiro,Matsusaki, Michiya,Akashi, Mitsuru. "Complete surface control of peptide nanospheres with detachable and attachable polymer brush layers". . p. 7025 - 7027. Retrieved 2010.
• 3、 Huang, Jin,Hastings, Conn L.,Duffy, Garry P.,Kelly, Helena M.,Raeburn, Jaclyn,Adams, Dave J.,Heise, Andreas. "Supramolecular hydrogels with reverse thermal gelation properties from (Oligo)tyrosine containing block copolymers". . p. 200 - 206. Retrieved 2013.
• 4、 Nagai, Atsushi,Sato, Daisuke,Ishikawa, Junichi,Ochiai, Bungo,Kudo, Hiroto,Endo, Takeshi. "A Facile Synthesis of N-Carboxyanhydrides and Poly(α-amino acid) Using Di-tert-butyltricarbonate". . p. 2332 - 2334. Retrieved 2004.
• 5、 Barrett, Stephanie E.,Abrams, Marc T.,Burke, Rob,Carr, Brian A.,Crocker, Louis S.,Garbaccio, Robert M.,Howell, Bonnie J.,Kemp, Eric A.,Kowtoniuk, Robert A.,Latham, Andrew H.,Leander, Karen R.,Leone, Anthony M.,Patel, Mihir,Pechenov, Sergey,Pudvah, Nicole T.,Riley, Sean,Sepp-Lorenzino, Laura,Walsh, Eileen S.,Williams, J. Michael,Colletti, Steven L.. "An in vivo evaluation of amphiphilic, biodegradable peptide copolymers as siRNA delivery agents". . p. 58 - 67. Retrieved 2014.
• 6、 Chen, Hongyi,Chen, Qinjun,Chu, Yongchao,Guo, Qin,Guo, Zhongyuan,Jiang, Chen,Jiang, Liping,Li, Chao,Liu, Peixin,Sun, Tao,Yu, Haijun,Zhang, Guangping,Zhang, Yiwen,Zhang, Yujie,Zhou, Wenxi. "Co-delivery of Cu(I) chelator and chemotherapeutics as a new strategy for tumor theranostic". . p. 483 - 496. Retrieved 2020/03/03.
• 7、 -. "METHOD FOR PRODUCING AMINO ACID-N-CARBOXYLIC ACID ANHYDRIDE". Paragraph 0063-0065; 0072. . Retrieved 2020/08/07.