175212-40-5

Usage

Uses

Used in Pharmaceutical Industry:
(4S)-(4-FLUOROPHENOXY)METHYL BUTYROLACTONE is used as a GABA receptor agonist for its potential anxiolytic and sedative effects, making it a candidate for the treatment of anxiety and other central nervous system disorders.
Used in Research and Development:
(4S)-(4-FLUOROPHENOXY)METHYL BUTYROLACTONE is used as a research compound to study its pharmacological properties and explore its potential therapeutic applications in the treatment of various conditions related to the central nervous system.

Upstream product

• 371-41-5 4-Fluorophenol 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 56-86-0 L-glutamic acid 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 

Downstream Products

• 175212-45-0 (2S,5S)-trans-5-(4-fluorophenoxymethyl)-5-(4-N,O-bis-(phenoxycarbonyl)hydroxylamino-3-butyn-4-yl)tetrahydrofuran 
• 220623-68-7 (5S)-5-(4-fluorophenoxymethyl)-2-(tert-butyldimethylsiloxy)tetrahydrofuran 
• 280122-85-2 (2RS,5S)-5-(4-fluorophenoxymethyl)-2-(but-3-yne-1-oxy)tetrahydrofuran 
• 220623-67-6 (2RS,5S)-5-(4-fluorophenoxymethyl)-2-hydroxytetrahydrofuran 

Relevant academic research and scientific papers

A short and efficient stereoselective synthesis of the potent 5- lipoxygenase inhibitor CMI-977

A short and efficient synthesis of the potent 5-lipoxygenase inhibitor CMI-977 is described using as the key step a stereoselective anomeric oxygen to carbon rearrangement of an alkynyl stannane tetrahydrofuranyl ether derivative mediated by boron trifluoride etherate.

Anomeric oxygen to carbon rearrangements of alkynyl tributylstannane derivatives of furanyl (γ)- and pyranyl (δ)-lactols

Tetrahydropyran and tetrahydrofuran containing natural products, drugs and agrochemicals often possess carbon-carbon bonds adjacent to the heteroatom. Consequently, new methods for the construction of anomeric carbon-carbon bonds are of considerable importance. We have devised a new strategy to access these systems that requires the treatment of O-glycoside alkynyl tributylstannane derivatives of furanyl and pyranyl lactols with Lewis acid to effect oxygen to carbon rearrangements. This leads to the formation of the corresponding carbon linked alkynol products that can be further manipulated to produce key structural motifs and building blocks for the assembly of complex molecules.

A short and efficient stereoselective synthesis of the potent 5-lipoxygenase inhibitor, CMI-977

A short and efficient synthesis of the potent 5-lipoxygenase inhibitor CMI-977 has been accomplished, utilising an oxygen to carbon rearrangement of an anomerically linked alkynyl stannane tetrahydrofuranyl ether derivative as the key step.

Synthesis of CMI-977, a potent 5-lipoxygenase inhibitor

CMI-977 is a potent 5-lipoxygenase inhibitor that intervenes in the production of leukotrienes and is presently being developed for the treatment of chronic asthma. It is a single enantiomer with an all-trans (2S,5S) configuration. Of the four isomers of CMI-977, the S,S isomer was found to have the best biological activity and was selected for further development. The enantiomerically pure product was synthesized on a 2-kg scale from (S)-(+)-hydroxymethyl-γ-butyrolactone.