37498-95-6

Basic information

• Product Name: (R)-4-BENZYL-OXAZOLIDINE-2,5-DIONE
• Synonyms: (R)-4-BENZYL-OXAZOLIDINE-2,5-DIONE
• CAS NO: 37498-95-6
• Molecular Formula: C₁₀H₉NO₃
• Molecular Weight: 191.18
• Mol File: 37498-95-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 90°C
• Appearance: /
• CAS DataBase Reference: (R)-4-BENZYL-OXAZOLIDINE-2,5-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-BENZYL-OXAZOLIDINE-2,5-DIONE(37498-95-6)
• EPA Substance Registry System: (R)-4-BENZYL-OXAZOLIDINE-2,5-DIONE(37498-95-6)

Safety Data

• Hazardous Substances Data: 37498-95-6(Hazardous Substances Data)

Usage

General Description

(R)-4-Benzyl-oxazolidine-2,5-dione, also known as D-mannitol benzyl oxazolidine-2,5-dione, is a chemical compound with the molecular formula C10H9NO3. It is mainly used as a precursor in the synthesis of various pharmaceuticals and agrochemicals. (R)-4-BENZYL-OXAZOLIDINE-2,5-DIONE is a chiral molecule and is widely used as a building block in the synthesis of enantiopure compounds. It can also be utilized as a chiral ligand in asymmetric catalysis. The (R)-4-Benzyl-oxazolidine-2,5-dione has potential applications in the pharmaceutical and agrochemical industries due to its versatile use as a chiral building block in the synthesis of active pharmaceutical ingredients and crop protection products.

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 63-91-2 L-phenylalanine 
• 75-44-5 phosgene 
• 673-06-3 D-(R)-phenylalanine 
• 503-38-8 trichloromethyl chloroformate 
• 28069-46-7 D-phenylalanine hydrochloride 

Downstream Products

• 462-60-2 N-carbamoylglycine 
• 22951-94-6 Phenylalanyl-isoleucin 
• 63-91-2 L-phenylalanine 
• 721-90-4 (S)-PheGly 
• 1795-96-6 D-phenylalanine ethyl ester 
• 94263-96-4 Ts-Gly-NH-NH-D-Phe 
• 99032-25-4 Bz-Gly-NH-NH-D-(CO-CH(NH₂)-CH₂-C₆H₅) 
• 3918-90-9 L-phenylalanyl-L-valine 

Relevant articles and documents

Large-scale synthesis of α-amino acid-N-carboxyanhydrides

Hetero- and homopolymers prepared from α-amino acid-N-carboxyanhydrides (NCAs) monomers are widely useful products. The preparation of pure NCA monomers has been extensively studied in the past. Purification methods including repeated crystallizations, extraction, and flash column chromatography have been devised. However, these methods are not easily amendable to large-scale NCA preparations. This article describes the synthesis of numerous highly purified NCAs on a >100 g scale using a simple filtration step through diatomaceous earth (celite). The resulting NCAs provided polyethylene glycol (PEG)–amino acid triblock polymers devoid of low-molecular-weight by-products that were routinely observed when unfiltered batches of NCAs were used. Also disclosed is the preparation of NCAs at ambient temperature. Traditionally, NCA reactions using a phosgene source are heated. This study shows these reactions can be driven by the slight exotherm that forms upon reagent mixing. This eliminates the need for an external heating source, simplifying large-scale reactions.

THE PREPARATION OF N-CARBOXYANHYDRIDES OF α-AMINO ACIDS USING BIS(TRICHLOROMETHYL)CARBONATE

A syntheis of the N-carboxyanhydrides (NCA's) of several α-amino acids using bis(trichloromethyl)carbonate, 1, is reported.The triphosgene is used to supply phosgene in situ in stoichiometric amounts; it is particularly effective for preparing NCA's of amino acids with long, aliphatic side chains.