36298-43-8

Basic information

• Product Name: (4S,5S)-3,4-dimethyl-2,5-diphenyl-1,3-oxazolidine
• CAS NO: 36298-43-8
• Molecular Formula: C₁₇H₁₉NO
• Molecular Weight: 253.3389
• Mol File: 36298-43-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 366.9°C at 760 mmHg
• Flash Point: 108.3°C
• Density: 1.059g/cm³
• Vapor Pressure: 1.41E-05mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: (4S,5S)-3,4-dimethyl-2,5-diphenyl-1,3-oxazolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5S)-3,4-dimethyl-2,5-diphenyl-1,3-oxazolidine(36298-43-8)
• EPA Substance Registry System: (4S,5S)-3,4-dimethyl-2,5-diphenyl-1,3-oxazolidine(36298-43-8)

Safety Data

• Hazardous Substances Data: 36298-43-8(Hazardous Substances Data)

Usage

Description

(4S,5S)-3,4-dimethyl-2,5-diphenyl-1,3-oxazolidine is a chiral oxazolidine molecule characterized by two asymmetric carbon centers. It is a cyclic organic compound that features a five-membered ring structure composed of oxygen and nitrogen atoms. (4S,5S)-3,4-dimethyl-2,5-diphenyl-1,3-oxazolidine is known for its unique structure and chirality, which make it a valuable asset in the field of organic chemistry.

Uses

Used in Organic Synthesis:
(4S,5S)-3,4-dimethyl-2,5-diphenyl-1,3-oxazolidine is utilized as a chiral auxiliary in organic synthesis to control the stereochemistry of reactions. It plays a crucial role in the formation of chiral alcohol and amine derivatives, ensuring the desired enantioselective outcomes are achieved.
Used in Drug Development:
Due to its unique structural properties, (4S,5S)-3,4-dimethyl-2,5-diphenyl-1,3-oxazolidine has been studied for its potential applications in drug development. Its chiral nature and ability to influence the stereochemistry of reactions make it a promising candidate for the creation of new pharmaceutical compounds.
Used as a Building Block in Pharmaceutical Compounds:
(4S,5S)-3,4-dimethyl-2,5-diphenyl-1,3-oxazolidine also serves as a building block for creating new pharmaceutical compounds. Its incorporation into the molecular structures of drugs can enhance their efficacy and selectivity, contributing to the advancement of medicinal chemistry.

Upstream product

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Downstream Products

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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.

Formation of azomethine ylids by thermolysis of oxazolidines. Study of the reaction in solution and in the gaseous phase

Thermolysis of oxazolidines leads to azomethine ylids via cycloreversion.In the liquid phase, these intermediates then give 1-3 dipolar cycloaddition; in the gaseous phase, they lead to aziridines.With an alkyl group in position 2, we observed also the formation of enamines.The effect of substituents on both the cycloreversion reaction and the evolution of azomethine ylids was studied.The mechanism of the process tautomerism aziridine -> azomethine ylid -> enamine is discussed.Keywords - azomethine ylids / oxazolidines / cycloreversion / aziridines / enamines / tautomerism