(R)-4-Benzyl-2-oxazolidinone(CAS#102029-44-7)
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 3-10 |
| HS Code | 29349990 |
Introduction
Insoluble in water
Application
(R)-4-Benzyl-2-oxazolidinone (CAS 102029-44-7) is a privileged chiral auxiliary developed by Evans, and it remains one of the most widely used tools for stoichiometric asymmetric synthesis. It enables highly stereocontrolled reactions, including enantioselective alkylation, aldol condensation, Diels-Alder cycloaddition, and acylation, with predictable product configurations and high diastereoselectivity (typically >95% de). The oxazolidinone ring acts as a rigid chiral template, directing facial selectivity during enolate formation and facilitating clean auxiliary removal for recycling. In drug discovery, (R)-4-Benzyl-2-oxazolidinone is a key precursor for HIV protease inhibitors (e.g., 1592U89), aromatase inhibitors for estrogen-dependent breast cancer research, and antiepileptic agents such as (R)-lacosamide. It is also integral to the synthesis of enantiopure carbocyclic nucleosides for antiviral studies, beta-lactam antibiotics, alpha-amino acids, and the total synthesis of complex natural products including Stereocalpin A and enantioselective methylphenidate (Ritalin). Beyond pharmaceuticals, this building block finds applications in asymmetric catalysis, agrochemical development, and advanced material science for specialty polymers and coatings. Xinchem is a leading manufacturer and supplier of high-purity (R)-4-Benzyl-2-oxazolidinone. We offer flexible custom synthesis, custom chemical synthesis, and reliable contract manufacturing to support your enantioselective synthesis programs. Contact us today for a competitive quote and trusted global supply.
