220623-71-2

Upstream product

• 253866-75-0 2-{4-[(S)-5-(4-Fluoro-phenoxymethyl)-tetrahydro-furan-2-yl]-but-3-ynyloxy}-tetrahydro-pyran 
• 280122-85-2 (2RS,5S)-5-(4-fluorophenoxymethyl)-2-(but-3-yne-1-oxy)tetrahydrofuran 
• 75-21-8 oxirane 
• 253866-88-5 (2S,5S)-2-ethynyl-5-[(4-fluorophenoxy)methyl]tetrahydrofuran 
• 254891-83-3 (5S)-5-((4-fluorophenoxy)methyl)-2-[1-(4-methoxybenzyloxy)-3-butyn-4-yl]tetrahydrofuran 
• 133008-09-0 (R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propanal 
• 36326-38-2 ethyl (R,Z)-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)acrylate 
• 133008-08-9 (4R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propan-1-ol 
• 173152-84-6 ethyl (R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propionate 
• 253867-31-1 (2S)-2-(hydroxymethyl)-5-[1-(4-methoxybenzyloxy)-3-butyn-4-yl]tetrahydrofuran 
• 851532-53-1 (2R)-5-hydroxy-1,2-(isopropylidenedioxy)-9-(4-methoxybenzyloxy)non-6-yne 
• 851532-55-3 (2R)-5-acetoxy-1,2-dihydroxy-9-(4-methoxybenzyloxy)non-6-yne 
• 851532-54-2 (2R)-5-acetoxy-1,2-(isopropylidenedioxy)-9-(4-methoxybenzyloxy)non-6-yne 
• 254891-82-2 (2S)-5-[1-(4-methoxybenzyloxy)-3-butyn-4-yl]-2-(p-toluenesulfonyloxy)tetrahydrofuran 

Downstream Products

• 175212-45-0 (2S,5S)-trans-5-(4-fluorophenoxymethyl)-5-(4-N,O-bis-(phenoxycarbonyl)hydroxylamino-3-butyn-4-yl)tetrahydrofuran 

Relevant academic research and scientific papers

Stereoselective total synthesis of the potent anti-asthmatic compound CMI-977 (LDP-977)

A short and efficient stereoselective total synthesis of CMI-977 (LDP-977), a potent and orally active anti-asthmatic compound, was developed. The key steps involve a highly diastereoselective Mukaiyama oxidative cyclization, which provides the trans-THF (tetrahydrofuran) unit and a Seyferth-Gilbert homologation to construct the triple bond in the target molecule. The synthesis of the key chiral building block was performed using Jacobsen hydrolytic kinetic resolution.

Stereoselective synthesis of chiral tetrahydrofurans with potent 5-LO inhibitory activity

Chiral glyceraldehydes have been exploited for the design of convenient and scalable synthetic approaches to chiral tetrahydrofurans, which have potential as potent 5-lipoxygenase (5-LO) inhibitors. The synthesis of all four possible stereoisomers by a general methodology is reported; wherein the chirons derived from the glyceraldehyde derivatives on reaction with homopropargyl ether, cyclization and further reactions gave the targets.

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 novel and simple asymmetric synthesis of CMI-977 (LDP-977): A potent anti-asthmatic drug lead

A practical gram scale asymmetric synthesis of CMI-977 is described. A tandem double elimination of an α-chlorooxirane and concomitant intramolecular nucleophilic substitution was used as the key step. Jacobsen hydrolytic kinetic resolution and Sharpless

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.

Substituted oxygen alicyclic compounds, including methods for synthesis thereof

The invention provides new methods for preparation of cyclic oxygen compounds, including 2,5-disubstituted tetahydrofurans, 2,6-disubstituted tetrahydropyrans, 2,7-disubstituted oxepanes and 2,8-oxocanes. The invention also provides new cyclic oxygen compounds and pharmaceutical compositions and therapeutic methods that comprise such compounds.

Methods for synthesis of substituted tetrahydrofuran compound

The invention includes inter alia new methods for preparation of the pharmaceutically active compound 2-(4-fluorophenoxymethyl)-5-(4-N-hydroxyureidyl-1-butynyl)-tetrahydrofuran and precursors thereof.

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.

A versatile approach to anti-asthmatic compound CMI-977 and its six- membered analogue

The synthesis of the anti-asthmatic compound CMI-977 is described. The tetrahydrofuran ring was effectively constructed by involving olefin metathesis while the stereoselective introduction of the 1-N- hydroxyureidylbut-3-yn-4-yl side-chain was achieved b

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.