N2 - A palladium-catalyzed Negishi coupling reaction has been developed to synthesize fluorous 5-methyl-cytosines. These fluorous nucleosides are incorporated into the oligonucleotides that correspond to part of the promoter region of Oct4, a master gene that undergoes dynamic DNA demethylation during cellular reprogramming. The separation of the fluorous oligonucleotides from its nonfluorous analogues has been achieved through solid-phase extraction over fluorous silica, suggesting its potential use in probing DNA demethylation (Figure presented).
Fluorous mixture synthesis (FMS) is a newly developed highly-efficient solution-phase technology. A set of substrates attached to homologous fluorous tags is mixed and taken through a sequence of organic reactions. The final mixtures are demixed by fluorous HPLC and detagged to give individually pure final products. Applications of FMS for the preparation of 2 enantiomers of pyridovericin, 16 diastereomers of murisolin, and a 560-member mappicine library are highlighted in this article.
Click Synthesis of Fluorine-Rich Cyclotriphosphazene Hydrazones.
224. B. Linclau and D. P. Curran, Fluorous Scavenging. In: High-Throughput Synthesis: Principles and Practices, (I. Sucholiecki, Ed.), Marcel Dekker, New York, 2001, 135.
Bare-Minimum Fluorous Mixture Synthesis of a …
In addition to the basic four fluorous deoxyribonucleoside phosphoramidites, fluorous versions of other nucleic acid synthesis reagents are in development.
Product List Fluorous Phase Organic Synthesis - Sigma …
The fluorous traceless synthesis of substituted indole alkaloids is carried out first by attaching the 3-(perfluorooctyl)propanol with Boc protected -tryptophan. The reaction of perfluoroalkyl (Rfh)-tagged tryptophan esters with various aldehydes undergos Pictet-Spengler reaction to give cis and trans stereoisomers of tetrahydro-β-carbolines. The nucleophilic addition of the piperidine nitrogen across various isocyanates is followed by the cyclization of ureas and simultaneous rupture of the fluorous tag to afford the hydantoin ring fused tetrahydro-β-carbolines. All the fluorous-tag compounds are purified by solid-phase extraction (SPE) through Fluoro cartridges.
FMS abbreviation stands for Fluorous Mixture Synthesis
and and and and and and and (2009)Fluorous parallel synthesis of a piperazinedione-fused tricyclic compound library. Journal of Combinatorial Chemistry, 11 (3). 452 - 459. ISSN 1520-4766
16.3.2 Recycling techniques in fluorous synthesis 444.
AB - A new method for oligosaccharide assembly that combines the advantages of one-pot synthesis and fluorous separation is described. After one-pot glycosylations are completed, a fluorous tag is introduced into the reaction mixture to selectively "catch" the desired oligosaccharide, which is rapidly separated from non-fluorous impurities by fluorous solidphase extraction (F-SPE). Subsequent "release" of the fluo-rous tag and F-SPE achieved the purification of the desired oligosaccharide without the use of time- and solvent-consuming silica gel chromatography. Linear and branched oligosaccharides have been synthesized with this approach in just a few hours (for the overall oligosaccharide assembly and purification process).