Benzyl(S)-2,5-dioxooxazolidine-4-acetate

• CAS: 13590-42-6
• Catalog Number: ACM13590426
• Category: Main Products
• Molecular Weight: 249.21944
• Molecular Formula: C₁₂H₁₁NO₅
• Synonyms: benzyl (S)-2,5-dioxooxazolidine-4-acetate;H-ASP(OBZL)-NCA;(4S)-2,5-Dioxooxazolidine-4-acetic acid benzyl ester;(4S)-4-(Benzyloxycarbonylmethyl)oxazolidine-2,5-dione;(4S)-4-[2-(Benzyloxy)-2-oxoethyl]oxazolidine-2,5-dione;(S)-2,5-Dioxo-4-oxazolidineacetic acid phenylmethyl ester;2-[(4S)-2,5-Dioxooxazolidine-4-yl]acetic acid benzyl ester;3-(Benzyloxycarbonyl)-N-carboxy-L-alanine anhydride
• IUPAC Name: benzyl2-[(4S)-2,5-dioxo-1,3-oxazolidin-4-yl]acetate
• Canonical SMILES: C1=CC=C(C=C1)COC(=O)CC2C(=O)OC(=O)N2
• InChI Key: QNIPTEJAZIWFHH-VIFPVBQESA-N
• Density: 1.332g/cm³
• EC Number: 237-026-9
• Exact Mass: 249.06400

Case Study

Benzyl(S)-2,5-Dioxooxazolidine-4-Acetate for the Preparation of Tumor-Specific Nanocarriers

Qi, Chao, et al. ACS nano, 2020, 15(1), 1627-1639.

This work reported the development of a tumor-specific, pH-responsive MnCO3 nanocarrier using PEG-b-PAsp as a template and a biomimetic mineralization method. Once activated by the acidic tumor microenvironment (TME), the nanocarrier has diagnostic and therapeutic functions suitable for tumor diagnosis and treatment. Among them, benzyl(S)-2,5-dioxooxazolidine-4-acetate was used in the preparation step of the PEG-b-PAsp template.
Preparation of PEG-b-PAsp
· A solution of 1.960 g benzyl (S)-2,5-dioxooxazolidine-4-acetate in 2.9 mL DMF and 29 mL CH₂Cl₂ was combined with a solution of 1.562 g mPEG-NH₂ in 3 mL DMF and 12 mL CH2Cl2. Ring-opening polymerization of the benzyl ester was initiated by adding the mPEG-NH2 solution and proceeding at 35 °C under argon for 48 hours. The resulting PEG-b-poly(β-benzyl-L-aspartate) (PEG-b-PBLA) block copolymer was isolated by precipitation in n-hexane and vacuum drying.
· To deprotect the benzyl groups, 3 g PEG-b-PBLA was dissolved in 30 mL DMSO and treated with 20 mL 1 M NaOH at room temperature for 24 hours. The reaction mixture was then dialyzed against deionized water for 24 hours and concentrated by centrifugal ultrafiltration (6000 rpm, 5 min). The final PEG-b-PAsp concentration for subsequent experiments was 16 mg/mL.

Benzyl(S)-2,5-Dioxooxazolidine-4-Acetate for Constructing a Functional Nanoplatform Based on Disulfiram Prodrug

Cheng, Fen-Ting, et al. Nanoscale Advances, 2023, 5(12), 3336-3347.

A functional nanoplatform based on disulfiram (DSF) prodrug was reported to fight cancer. Based on Benzyl(S)-2,5-dioxooxazolidine-4-acetate (BLA-NCA), peptides were prepared by ring-opening polymerization, which were further modified with PEG-NH2 to obtain mPEG-b-PBLA. Subsequently, DSF prodrug was introduced into the nanoplatform through B-N coordination to form Cu@P-B NPs to obtain amphiphilic polymers. The functional Cu@P-B NPs release the encapsulated DSF prodrug and CuO2 NPs in the tumor microenvironment.
Synthesis of mPEG-b-PNAEA from BLA-NCA
· BLA-NCA (398.8 mg, 1.6 mmol) was dissolved in dry THF (16.0 mL) and mixed with a 1.0 M solution of lithium bis(trimethylsilyl)amide (LiHMDS) in THF (0.2 mL, 0.2 mmol) at room temperature while stirring.
· The resulting reaction mixture was stirred at room temperature for three hours before adding mPEG-NH2 (600 mg, 0.2 mmol), which had been dissolved in dry THF, and the mixture was stirred overnight.
· Following the reaction, mPEG-b-PBLA was precipitated from an excess of methanol. The obtained mPEG-b-PBLA was then dissolved in DMF (10 mL), to which ethylenediamine (1.0 mL) was added. This mixture was kept at room temperature for ten hours.
· After the reaction was complete, purification was carried out by dialysis (MWCO, 1000 Da) against methanol for 24 hours. Most of the solvent was then removed using rotary evaporation, and mPEG-b-PNAEA was obtained by precipitation with excess diethyl ether and concentrated under vacuum.

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Synthetic Use

Upstream Synthesis Route 1

• 32315-10-9
• 2177-63-1

• 13590-42-6

Reference: [1] Journal of Drug Delivery Science and Technology, 2018, vol. 45, p. 281 - 286

Upstream Synthesis Route 2

• 2177-63-1
• 503-38-8

• 13590-42-6

Reference: [1] Synthetic Communications, 2017, vol. 47, # 1, p. 53 - 61
[2] Journal of Organic Chemistry, 1985, vol. 50, # 5, p. 715 - 716
[3] Acta Crystallographica Section C: Crystal Structure Communications, 2003, vol. 59, # 3, p. o159-o161

Upstream Synthesis Route 3

• 79-37-8
• 130529-78-1

• 13590-42-6

Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 12, p. 2200 - 2202

Upstream Synthesis Route 4

• 3479-47-8

• 13590-42-6

Reference: [1]Journal of Organic Chemistry,1951,vol. 16,p. 1513,1516

Upstream Synthesis Route 5

• 75-44-5
• 2177-63-1

• 13590-42-6

Reference: [1]Chemistry - A European Journal,2018,vol. 24,p. 14373 - 14377
[2]Archiv der Pharmazie,2006,vol. 339,p. 283 - 290
[3]Archiv der Pharmazie,2001,vol. 334,p. 189 - 193
[4]Bulletin de la Societe Chimique de France,1971,p. 4387 - 4391

Downstream Synthesis Route 1

• 7669-54-7
• 13590-42-6

• 54743-91-8

Reference: [1]Chemische Berichte,1974,vol. 107,p. 3533 - 3547
[2]Journal of Organic Chemistry,1975,vol. 40,p. 2697 - 2702

* For details of the synthesis route, please refer to the original source to ensure accuracy.