220623-67-6

Usage

Uses

Used in Organic Synthesis:
(2RS,5S)-5-(4-fluorophenoxymethyl)-2-hydroxytetrahydrofuran is utilized as a building block in organic synthesis, providing a versatile structure that can be further modified to create a range of different organic compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (2RS,5S)-5-(4-fluorophenoxymethyl)-2-hydroxytetrahydrofuran is used as a key intermediate in the synthesis of biologically active compounds. Its unique structure, including the presence of a fluorine atom in the phenoxymethyl group, may enhance the reactivity and biological activity of the resulting pharmaceuticals, making it a valuable component in drug development.
Used in the Development of New Pharmaceuticals:
(2RS,5S)-5-(4-fluorophenoxymethyl)-2-hydroxytetrahydrofuran is of particular interest in the development of new pharmaceuticals due to its potential to influence the properties of the compounds it is used to synthesize. Its chirality and structural features make it a promising candidate for creating innovative and effective medications.

Upstream product

• 56-86-0 L-glutamic acid 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 371-41-5 4-Fluorophenol 
• 175212-40-5 (5S)-5-(4-fluorophenoxymethyl)-γ-butyrolactone 

Downstream Products

• 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 

Relevant academic research and scientific papers

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.

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.

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.