123618-06-4

Usage

Uses

Used in Organic Synthesis:
(4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine is utilized as a key intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique structure and reactivity make it a valuable building block for the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Catalysis:
In the field of catalysis, (4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine serves as a chiral catalyst or ligand, facilitating asymmetric reactions and enhancing the selectivity of chemical transformations. Its stereochemistry plays a crucial role in determining the enantioselectivity and efficiency of catalytic processes.
Used in Pharmaceutical Chemistry:
(4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine is employed as a potential pharmaceutical agent or as a precursor for the development of new drugs. Its unique structure and biological activity make it a candidate for the treatment of various diseases, including infectious diseases, neurological disorders, and cancer.
Used in Chiral Pool Synthesis:
(4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine is used as a chiral building block in the synthesis of enantiomerically pure compounds. Its specific stereochemistry allows for the creation of chiral centers in target molecules, which is essential for the development of enantioselective synthetic routes and the production of single-enantiomer pharmaceuticals.
Used in Material Science:
In material science, (4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine can be used as a component in the design and synthesis of novel materials with specific properties, such as chiral polymers, liquid crystals, or self-assembling systems. Its unique structure and functional groups contribute to the development of materials with tailored properties for various applications, including sensors, catalysts, and drug delivery systems.

Upstream product

• 50-00-0 formaldehyd 
• 299-42-3 ephedrine 
• 1806-29-7 2,2'-dihydroxybiphenyl 
• 75-09-2 dichloromethane 
• 74-95-3 1,1-dibromomethane 
• 1047392-28-8 methyl 2-(N-acetylamino)-5-ethynylbenzoate 
• 90-81-3 ephedrine 
• 90-82-4 rac-pseudoephedrine 

Downstream Products

• 123387-83-7 (1R,2S)-2-[Methyl-(5-methyl-furan-2-ylmethyl)-amino]-1-phenyl-propan-1-ol 
• 23588-51-4 2,2-dimethyl-3-(N-morpholino)propanal 
• 76503-78-1 3,4,6,6-Tetramethyl-7-morpholino-2-phenylhexahydro-1,4-oxazepin 
• 15451-14-6 3-dimethylamino-2,2-dimethylpropanal 
• 76503-82-7 3,4,6,6-Tetramethyl-7-dimethylamino-2-phenylhexahydro-1,4-oxazepin 
• 76503-94-1 (2R, 4S, 5R)-2-Isopropenyl-3,4-dimethyl-5-phenyl-1,3-oxazolidin 
• 76503-95-2 (2S, 4S, 5R)-2-Isopropenyl-3,4-dimethyl-5-phenyl-1,3-oxazolidin 
• 76503-87-2 (2R, 3S)-c-7-Dimethylamino-3,4,r-6-trimethyl-2-phenylhexahydro-1,4-oxazepin 
• 76503-86-1 (2R, 3S)-3,4,6-Trimethyl-7-morpholino-2-phenylhexahydro-1,4-oxazepin 
• 50-47-5 desipramine 
• 462871-39-2 {[((1S,2R)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amino]-methyl}-phosphonic acid diethyl ester 
• 462871-54-1 {[((1S,2R)-2-Chloro-1-methyl-2-phenyl-ethyl)-methyl-amino]-methyl}-phosphonic acid diethyl ester 
• 462871-70-1 ((2R,3S,4S)-1,4-Dimethyl-3-phenyl-azetidin-2-yl)-phosphonic acid diethyl ester 
• 552-79-4 (-)-N-methylephedrine 

Relevant academic research and scientific papers

Condensation of chiral 1,3-oxazolidines with cathecol and 4,4'- dibromobiphenol: New enantiopure polydentate ligands with C2-symmetry

The new enantiopure polydentate ligands 3a,c and 4a-c have been synthesized via Mannich condensation of 1,3-oxazolidines 1a-c with 5,5'- dibromobiphenol and cathecol. The products are enantiopure C2 chiral ligands of potential use in asymmetric synthesis as well as bioactive compounds.

Stability studies of oxazolidine-based compounds using 1H NMR spectroscopy

A series of oxazolidine-based compounds with a variety of substituents in positions 2 and 3 was synthesized and their stability studied. Ring opened intermediates formed on addition of limiting amounts of D2O to oxazolidine solutions, as observ

Study of alkaloids of the Siberian and Altai flora 14. Synthesis of alkaloid-based tertiary N-(3-arylprop-2-ynyl)amines

3-Arylprop-2-ynylamines containing the key fragment of known alkaloids of the Altai flora were synthesized by the Sonogashira and Mannich reactions.

An efficient asymmetric synthesis of azetidine 2-phosphonic acids

Substituted azetidinic 2-phosphonates were prepared in diastereoisomerically and enantiomerically pure form, starting from readily available β-amino alcohols. This synthesis involved a three-step sequence: (i) N-alkylation of the starting amino alcohol wi

Reaction of 3-methylamino-1,2-diols with dihalomethanes. Synthesis of chiral 4-substituted 3-methyltetrahydro-1,3-oxazin-5-ols

Enantiomerically pure 4,5-disubstituted 3-methyltetrahydro-1,3-oxazines have been obtained by reaction of 3-methylamino-1,2-diols with dichloromethane by regioselective differentiation of hydroxyl groups. (C) 2000 Published by Elsevier Science Ltd.

The solid-state diastereoselective formation of oxazolidines

A number of organic and organometallic aldehydes have been converted into optically active oxazolidines by solid-state interaction with (-)-ephedrine and (+)-pseudoephedrine. The stereoselectivity of the solid-state reaction is compared with that in boili

The functionalisation of electron rich aromatic compounds with 1,3-oxazolidines and 1,3-dimethylimidazolidine

N-Phenyl- and N-alkyl-oxazolidines react with alkyl chlorosilanes in the presence of electron rich aromatic compounds with the formation of the expected Mannich bases: 2-methoxycarbonyl-3-methyloxazolidine also reacts with 2-methylfuran in the presence of thionyl chloride to give an a-amino acid derivative: the iminium salt derived from 1,3-dimethylimidazolidine was also shown to react with 2-methylfuran.

Prodrugs as drug delivery systems. XXV: Hydrolysis of oxazolidines - A potential new prodrug type

The hydrolysis kinetics of several oxazolidines derived from (-)-ephedrine and various aldehydes and ketones were studied to assess their suitability as prodrug forms for β-amino alcohols and/or carbonyl-containing compounds. The oxazolidines were found to undergo a facile and complete hydrolysis in the pH range of 1-11 at 37°. The hydrolysis rates were subject to general acid-base catalysis by buffer substances and depended strongly on pH. Most oxazolidines showed sigmoidal pH-rate profiles with maximum rates at pH > 7-7.5. At pH 7.40 and 37° the following half-lives of hydrolysis for the various ephedrine oxazolidines were found: 5 sec (formaldehyde), 18 sec (propionaldehyde), 5 min (benzaldehyde), 5 sec (salicylaldehyde), 30 min (pivalaldehyde), 4 min (acetone), and 6 min (cyclohexanone). The reaction rates in neutral and basic solutions were shown to decrease with increasing steric effects of the substituents derived from the carbonyl component and to decrease with increasing basicity of the oxazolidines. The oxazolidines are weaker bases (pK(a) 5.2-6.9) than the parent β-amino alcohol and more lipophilic at physiological pH. It is suggested that oxazolidines can be considered as potentially useful prodrug candidates for drugs containing a β-amino alcohol moiety or carbonyl groups.