Selectfluor: Mechanistic Insight and Applications

Nyffeler, Paul T.; Durón, Sergio G.; Burkart, Michael D.; Vincent, Stéphane; Wong, Chi‐Huey

doi:10.1002/chin.200516254

Cited by 33 publications

(47 citation statements)

References 1 publication

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“…16 following the procedure developed in our laboratory (Scheme 5). 7 The starting material was totally consumed after 24 hours with concomitant formation of products of very different polarity as judged by thin layer chromatography.…”

Section: Resultsmentioning

confidence: 99%

A convergent approach for the synthesis of fluorinated sphingosine analogues

Teare¹,

Huguet²,

Tredwell³

et al. 2007

Arkivoc

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An improved route to a fluorinated analogue of sphingosine has been developed starting from Garner's aldehyde with two cross-metathesis couplings and an electrophilic fluorodesilylation as the key steps. This approach eliminates the problem of double bond transposition encountered with strategies relying on the nucleophilic fluorinating reagent DAST and supplies the target compound as well as a fluorinated intermediate amenable to functional variations at three sites.

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Section: Resultsmentioning

confidence: 99%

A convergent approach for the synthesis of fluorinated sphingosine analogues

Teare¹,

Huguet²,

Tredwell³

et al. 2007

Arkivoc

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“…Selectfluor (288) is one of the most reactive electrophilic fluorination reagents and is safe, nontoxic, and easy to handle. 155 As such, 288 represents a significant advance in preparative organofluorine chemistry. The preparation This methodology has been translated onto a commercially available automated synthesis unit that has produced quantities of [ 18 F]-labeled PET radioligands suitable for use in imaging studies.…”

Section: Perspectivementioning

confidence: 99%

Applications of Fluorine in Medicinal Chemistry

et al. 2015

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The role of fluorine in drug design and development is expanding rapidly as we learn more about the unique properties associated with this unusual element and how to deploy it with greater sophistication. The judicious introduction of fluorine into a molecule can productively influence conformation, pKa, intrinsic potency, membrane permeability, metabolic pathways, and pharmacokinetic properties. In addition, (18)F has been established as a useful positron emitting isotope for use with in vivo imaging technology that potentially has extensive application in drug discovery and development, often limited only by convenient synthetic accessibility to labeled compounds. The wide ranging applications of fluorine in drug design are providing a strong stimulus for the development of new synthetic methodologies that allow more facile access to a wide range of fluorinated compounds. In this review, we provide an update on the effects of the strategic incorporation of fluorine in drug molecules and applications in positron emission tomography.

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“…15 LgtC and OtsA are both retaining glycosyltransferases. The 2-deoxy-2-fluoro-sugar-nucleotides have been shown to inhibit a broad range of GTs: mammalian sialyl-T, human Fuc-T, bovine α or β-Gal-T. 21,22 From a biocatalytic point of view, these species are considered as useful mechanistic probes to identify the formation of cationic high-energy intermediates. In this case, given the similar values of the inhibitory activity of ADP-2F-heptose and the K m of ADPheptose, one can reasonably conclude that these two molecules bind WaaC in a very similar fashion, despite the reversal of configuration at the 2 position.…”

Section: Sugar Donor-binding Sitementioning

confidence: 99%