406463-50-1

Usage

Uses

Used in Pharmaceutical Industry:
(2S,4S)-4-hydroxy-2-methyl-4-[2-(1-methyl-2-oxoindolin-5-ylthio)thien-4-yl]-tetrahydropyran is used as a potential pharmaceutical candidate for various applications due to its complex structure and multiple functional groups. Its specific stereochemistry and the presence of a tetrahydropyran ring, thienylthio group, and oxoindolinylthio group may contribute to its pharmacological or biological activities, which could be harnessed for the development of new drugs.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (2S,4S)-4-hydroxy-2-methyl-4-[2-(1-methyl-2-oxoindolin-5-ylthio)thien-4-yl]-tetrahydropyran serves as a subject of study for understanding its potential interactions with biological targets. (2S,4S)-4-hydroxy-2-methyl-4-[2-(1-methyl-2-oxoindolin-5-ylthio)thien-4-yl]-tetrahydropyran's structure may provide insights into the design of new molecules with improved therapeutic properties, contributing to the advancement of drug discovery efforts.

Upstream product

• 166883-20-1 1-methyl-2-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride 
• 61-70-1 N-methyl-2-indolinone 
• 166883-22-3 5-mercapto-1-methylindolin-2-one 
• 166883-21-2 di-(1-methyl-2-oxoindolin-5-yl) disulphide 
• 3140-92-9 2,4-dibromothiophene 
• 82110-21-2 (S)-2-methyl-3,4,5,6-tetrahydro-2H-pyran-4-one 
• 851724-01-1 1-methyl-5-thiocyanato-1,3-dihydro-indol-2-one 

Relevant academic research and scientific papers

Efficient syntheses of AZD4407 via thioether formation by nucleophilic attack of organometallic species on sulphur

The development of two efficient strategies for the synthesis of AZD4407 is reported, both of which are considered suitable for large-scale manufacture. In the first approach, 3-bromothiophene is coupled with (2S)-2- methyltetrahydropyran-4-one using Grignard chemistry. Following hydroxyl protection and lithiation at thiophene C-2, reaction with a protected 5-mercapto-1-methyl-1,3-dihydro-indol-2-one derivative bearing a leaving group on sulphur provides AZD4407 after acid-catalysed deprotection and epimerisation. The second approach starts from 2,4-dibromothiophene, which undergoes a selective Grignard exchange reaction at C-2 followed by reaction with similar protected mercapto-oxindole derivatives. Reprotection of the oxindole ring, followed by a second Grignard exchange, and reaction with (2S)-2- methyltetrahydropyran-4-one provides AZD4407 after acid-catalysed deprotection and epimerisation.