Organofluorine compounds and fluorinating agents

Schwäbisch, Dirk; Hein, Martin; Miethchen, Ralf

doi:10.1016/j.jfluchem.2003.11.006

Cited by 10 publications

(10 citation statements)

References 24 publications

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“…[45][46][47] and papers cited therein. Dithionitemediated perfluoroalkylations, bromodifluoromethylations and chlorodifluoromethylations were carried out with allyl ethers of carbohydrates [48][49][50], glycals [43a,51-53] and allylated inositols [54]; (see also ref. [48]).…”

Section: C-fluoroalkylations Of Carbohydrate Derivatives With 1-halogmentioning

confidence: 99%

“…These reactions proceed via perfluoroalkyl radicals or radical anions. We have reported about S-perfluoroalkyl thioglycosides obtained by dithionite-mediated perfluoroalkylation of 1-thio-D-glucose and i = CF 3 ZnBr ·2MeCN (CH 2 Cl 2 ), r.t., 6-8 h; ii = CF 3 COOH (80%), r.t., 10 1-thio-D-galactose derivatives [48,54]. Scheme 10 shows two examples.…”

Section: S-perfluoroalkylation Of Thiosugarsmentioning

confidence: 99%

“…Treatment of compound 54 with the classical deacetylation reagent MeOH/NaOMe has shown that the perfluoroalkylthio group was replaced in a transglycosylation reaction forming methyl D-glucoside 57. Additionally, the orthoester derivative 56 was isolated, i.e., the two a-fluorine atoms of the perfluoroalkyl chain were replaced by methoxy groups [54]; Scheme 10.…”

Section: S-perfluoroalkylation Of Thiosugarsmentioning

confidence: 99%

“…Such derivatives were only accessible by application of a new three component reaction first reported by our group. The one pot method, described in detail in a recent review [16], allows acetalization of carbohydrates or inositols with perfluoroalkanals [55][56][57], perfluoroalkanal methylhemiacetals [54,56], or hexafluoroacetone [58] in the presence of a carbodiimide as co-reagent. The reaction is always accompanied by selective epimerization of the sugar and inositol, respectively, as shown by selected examples in Scheme 11.…”

Section: Epimerization By Non-conventional Acetalizationmentioning

confidence: 99%

“…The practicability of the method for inositols is demonstrated by the third example in Scheme 11. (-)-chiro-Inositol derivative 64 reacts with perfluoroheptanal methylhemiacetal/ DCC to myo-inositol acetal 65 [54]. Thus, it may be generalized that all cyclic triols (or tetrols) with contiguous hydroxyl groups in a cis-trans sequence are suitable starting materials for this acetalization procedure [16,55].…”

Section: Epimerization By Non-conventional Acetalizationmentioning

confidence: 99%

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Modified natural substances—fluorinated and fluoroalkylated monosaccharides and inositols

Miethchen

2004

Journal of Fluorine Chemistry

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Section: C-fluoroalkylations Of Carbohydrate Derivatives With 1-halogmentioning

confidence: 99%

Section: S-perfluoroalkylation Of Thiosugarsmentioning

confidence: 99%

Section: S-perfluoroalkylation Of Thiosugarsmentioning

confidence: 99%

Section: Epimerization By Non-conventional Acetalizationmentioning

confidence: 99%

Section: Epimerization By Non-conventional Acetalizationmentioning

confidence: 99%

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Modified natural substances—fluorinated and fluoroalkylated monosaccharides and inositols

Miethchen

2004

Journal of Fluorine Chemistry

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Approaches to the Synthesis of Perfluoroalkyl‐Modified Carbohydrates and Derivatives: Thiosugars, Iminosugars, and Tetrahydro(thio)pyrans

Uhrig

Flores

Postigo

2021

Chemistry A European J

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Fluoroalkyl-substituted carbohydrates play relevant roles in diverse areas such as supramolecular chemistry, glycoconjugation, liquid crystals, and surfactants, with direct applications as wetting, antifreeze, and coating agents. In light of these promising applications, new methodologies for the late-stage incorporation of fluoroalkyl R F groups into carbohydrates and derivatives are herein presented as they are relevant to the synthetic carbohydrate community. Previously reviewed protocols for the installation of R F groups onto carbohydrates and derivatives will be succinctly summarized in the light of the new achievements. Fluoroalkylsubstituted iminosugars, on the other hand, are also interesting glycomimetic derivatives with prominent roles as glycosidases and glycosyltransferases inhibitors, as has recently been demonstrated. Also, they positively contribute to the study of sugar-protein interactions and enzyme mechanisms. New advances in the syntheses of fluoroalkyl-substituted iminosugars will also be presented here.

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