29843-09-2

Basic information

• Product Name: (2R,4S,5R)-3,4-dimethyl-2,5-diphenyloxazolidine
• Synonyms: (2R,4S,5R)-3,4-dimethyl-2,5-diphenyloxazolidine
• CAS NO: 29843-09-2
• Molecular Weight: 253.344
• Mol File: 29843-09-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (2R,4S,5R)-3,4-dimethyl-2,5-diphenyloxazolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4S,5R)-3,4-dimethyl-2,5-diphenyloxazolidine(29843-09-2)
• EPA Substance Registry System: (2R,4S,5R)-3,4-dimethyl-2,5-diphenyloxazolidine(29843-09-2)

Safety Data

• Hazardous Substances Data: 29843-09-2(Hazardous Substances Data)

Upstream product

• 299-42-3 ephedrine 
• 100-52-7 benzaldehyde 
• 321-98-2 (1S,2R)-(+)-ephedrine 
• 100-47-0 benzonitrile 
• 90-82-4 rac-pseudoephedrine 

Downstream Products

• 128257-18-1 (R)-N-Methyl-1-phenylpropylamine 
• 5933-40-4 (R)-(+)-N,α-dimethylbenzylamine 

Relevant articles and documents

From solution to in-cell study of the chemical reactivity of acid sensitive functional groups: A rational approach towards improved cleavable linkers for biospecific endosomal release

pH-Sensitive linkers designed to undergo selective hydrolysis at acidic pH compared to physiological pH can be used for the selective release of therapeutics at their site of action. In this paper, the hydrolytic cleavage of a wide variety of molecular structures that have been reported for their use in pH-sensitive delivery systems was examined. A wide variety of hydrolytic stability profiles were found among the panel of tested chemical functionalities. Even within a structural family, a slight modification of the substitution pattern has an unsuspected outcome on the hydrolysis stability. This work led us to establish a first classification of these groups based on their reactivities at pH 5.5 and their relative hydrolysis at pH 5.5 vs. pH 7.4. From this classification, four representative chemical functions were selected and studied in-vitro. The results revealed that only the most reactive functions underwent significant lysosomal cleavage, according to flow cytometry measurements. These last results question the acid-based mechanism of action of known drug release systems and advocate for the importance of an in-depth structure-reactivity study, using a tailored methodology, for the rational design and development of bio-responsive linkers.

Heterogeneous rhodium-catalyzed hydrogenation conditions for the highly effective synthesis of 1,3-oxazolidines from 1,2-amino alcohols and nitriles

A procedure easily to carried out for the synthesis of 1,3-oxazolidines in high yields using 1,2-amino alcohols, nitriles, an atmospheric pressure of hydrogen and catalytic quantities of rhodium on carbon powder is presented. This reaction probably involves the semi-hydrogenation of the nitrile followed by condensation with the amine alcohol. The process may constitute the key step in a two-step sequence for reducing a nitrile into the corresponding aldehyde.

STEREOCHEMISTRY-60 KINETIC CONTROL OF ASYMMETRIC INDUCTION DURING OXAZOLIDINE FORMATION FROM (-)-EPHEDRINE AND AROMATIC ALDEHYDES

Kinetically controlled oxazolidine formation was observed with aromatic aldehydes substituted by electron-withdrawing groups.The stereoselectivity is solvent dependent: non-stereoselective ring closure occurred in chloroform while a high diastereodifferentiation was observed in methanol.The first oxazolidine showing an unambiguous 2R configuration was synthesized from p-bromobenzaldehyde and (-)-ephedrine in alcohol medium.A mechanism involving a nucleophilic assistance by alcoholic solvents is suggested in order to clarify the differences in stereoselectivity.