741719-53-9

Usage

Uses

Used in Organic Synthesis:
(R)-4-[4-(Oxiranylmethoxy)-1,2,5-thiadiazol-3-yl]morpholine is used as a synthetic building block for the creation of more complex organic molecules. Its unique structure allows it to participate in a range of chemical reactions, such as nucleophilic substitutions, ring-opening reactions, and cross-coupling reactions, which can lead to the formation of novel compounds with diverse applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-4-[4-(Oxiranylmethoxy)-1,2,5-thiadiazol-3-yl]morpholine is used as a key intermediate in the synthesis of various drug candidates. Its ability to form a wide array of chemical bonds and its compatibility with different functional groups make it a valuable component in the development of new medications, particularly those targeting specific biological pathways or receptors.
Used in Chemical Research:
(R)-4-[4-(Oxiranylmethoxy)-1,2,5-thiadiazol-3-yl]morpholine is also utilized in academic and industrial research settings as a model compound for studying various chemical reactions and mechanisms. Its unique structure provides researchers with an opportunity to explore new reaction pathways, develop innovative synthetic strategies, and gain insights into the reactivity of similar compounds.
Used in Material Science:
In the field of material science, (R)-4-[4-(Oxiranylmethoxy)-1,2,5-thiadiazol-3-yl]morpholine can be employed as a component in the development of new materials with specific properties. Its incorporation into polymers, for instance, may lead to materials with enhanced thermal stability, mechanical strength, or chemical resistance, depending on the desired application.

InChI:InChI=1/C9H13N3O3S/c1-3-13-4-2-12(1)8-9(11-16-10-8)15-6-7-5-14-7/h7H,1-6H2/t7-/m1/s1

Upstream product

• 30165-97-0 3-hydroxy-4-(N-morpholino)-1,2,5-thiadiazole 
• 113826-06-5 (R)-glycidyl tosylate 
• 115314-14-2 (R)-glycidyl nosylate 
• 110638-00-1 3-chloro-1-<(4-morpholino-1,2,5-thidiazol-3-yl)oxy>-2-propanol 
• 58827-68-2 4-{4-[(2R/S)-oxiran-2-ylmethoxy]-1,2,5-thiadiazol-3-yl}morpholine 
• 67843-74-7 (S)-epichlorohydrin 
• 30165-96-9 3-Morpholino-4-chloro-1,2,5-thiadiazole 

Relevant academic research and scientific papers

A smart library of epoxide hydrolase variants and the top hits for synthesis of (S)-β-blocker precursors

Microtuning of the enzyme active pocket has led to a smart library of epoxide hydrolase variants with an expanded substrate spectrum covering a series of typical β-blocker precursors. Improved activities of 6- to 430-fold were achieved by redesigning the active site at two predicted hot spots. This study represents a breakthrough in protein engineering of epoxide hydrolases and resulted in enhanced activity toward bulky substrates. Hot pockets: Microtuning of the enzyme active pocket gives a smart library of epoxide hydrolase variants with an expanded substrate spectrum covering a series of typical β-blocker precursors. Improved activities of 6- to 430-fold were achieved by redesigning the active site at two predicted hot spots, and enhanced activity toward bulky substrates was found.

Process for preparing R-(+)-3-morpholino-4-(3- tert-butylamino-2-hydroxypropoxy)-1,2,5-thiadiazole

The present invention provides a process for preparing optically active timolol. The process comprises the following steps. Firstly, reacting 3-hydroxy-4-morpholino-1,2,5-thiadiazole with an optically active epichlorohydrin in the presence of a solvent system, which has a first volume and a catalyst optionally in the presence of a suitable base to obtain an optically active intermediate product. Secondly, treating the optically active intermediate product with a solution, which has a second volume and comprises tert-butylamine to obtain an optically active timolol. The solvent system used in the first step can be an amide solvent, sulfoxide solvent, cyclic hydrocarbon solvent, ketone solvent, or a heterocyclic solvent. The catalyst used in the first step can be an alkali metal hydroxide, alkali metal carbonate, alkali metal hydrogen carbonate, piperidine, pyridine, triethylamine, potassium hydroxide, sodium hydroxide, potassium carbonate, and other heterocyclic bases.

Enantioselective synthesis of (S)-timolol via kinetic resolution of terminal epoxides and dihydroxylation of allylamines

An efficient enantioselective synthesis of (S)-timolol has been described using chiral Co-salen-catalyzed kinetic resolution of less expensive (±)-epichlorohydrin with 3-hydroxy-4-(N-morpholino)-1,2,5-thiadiazole in good overall yield (55%) and excellent enantioselectivity (98%). Synthesis of (S)-timolol has also been achieved using hydrolytic kinetic resolution as well as asymmetric dihydroxylation routes in 90% ee and 56% ee, respectively.

Biocatalytic asymmetric synthesis of (S)- and (R)-Timolol

A new biocatalytic route for the synthesis of both enantiomers of Timolol (1) is described. Starting from 3,4-dichloro-1,2,5-thiadiazole (2), (R)- and (S)-Timolol (87% ee) were obtained in 35% and 30% overall yield, respectively. Asymmetric reduction of the intermediate haloketone 5 with baker's yeast afforded the corresponding halohydrin 6 in the optically active form (87% ee), which gave the R enantiomer (distomer) of Timolol. The S enantiomer (eutomer) was obtained via inversion of configuration of the halohydrin following the Mitsunobu procedure.

Arenesulfonate Derivatives of Homochiral Glycidol: Versatile Chiral Building Blocks for Organic Synthesis

The preparation of a series of crystalline arenesulfonate derivatives of enantiomerically enriched glycidol is described.The enhancement of optical purity by recrystallization was particularly successful for two of these derivatives, glycidyl tosylate and glycidyl 3-nitrobenzenesulfonate, which were obtained in 97 percent ee and 99 percent ee, respectively.Very high regioselectivity was observed in the reactions of these compounds with a variety of nucleophiles, including aryl oxides, Et2AlCN, organometallic reagents, and BH3-NaBH4.The application of this methodology to the synthesis of homochiral β-adrenergic blocking agents and homochiral terminal epoxides is discussed.