Journal ArticleDOI
Synthesis of α-CF2-mannosides and Their Conversion to Fluorinated Pseudoglycopeptides
TLDR
A methodology allowing the synthesis alpha-CF(2)-mannosides, based on the addition of a difluoroenoxysilane to a glycal followed by a dihydroxylation reaction, is described, which converts into two pseudoglycopeptides which may act as E- and P-selectin inhibitors.Abstract:
A methodology allowing the synthesis alpha-CF(2)-mannosides, based on the addition of a difluoroenoxysilane to a glycal followed by a dihydroxylation reaction, is described. The resulting 2,2-difluoro-2-mannosylacetate is converted into two pseudoglycopeptides which may act as E- and P-selectin inhibitors.read more
Citations
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Recent Advances in the Chemical Synthesis of C-Glycosides
TL;DR: Mechanistically, C-glycosylation reactions can involve glycosyl electrophilic/cationic species, anionic species, radical species, or transition-metal complexes, which are discussed as subcategories under each type of sugar precursor.
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Recent Developments in the Ferrier Rearrangement
TL;DR: A review of recent developments in the use of promoters for the Ferrier rearrangement of O-, N-, C- and S-nucleophiles with glycals can be found in this paper.
Journal ArticleDOI
Fluorinated enol ethers: their synthesis and reactivity
TL;DR: The present review lists different methods for the preparation of fluorinated enol ethers, and sums up their numerous synthetic applications.
Journal ArticleDOI
Fluoro-C-glycosides and fluoro-carbasugars, hydrolytically stable and synthetically challenging glycomimetics.
TL;DR: This review summarizes the studies devoted to the synthesis offluoro-C-glycosides and fluoro-carbasugars as well as the studies regarding their conformational behaviour and their potential as carbohydrate analogues.
Journal ArticleDOI
Design, synthesis and biological evaluation of mannosyl triazoles as FimH antagonists.
Oliver Schwardt,Said Rabbani,Margrit Hartmann,Daniela Abgottspon,Matthias Wittwer,Simon Kleeb,Adam Zalewski,Martin Smieško,Brian Cutting,Beat Ernst +9 more
TL;DR: To address the druglikeness of this new class of FimH antagonists, selected pharmacokinetic parameters, which are critical for oral bioavailability (lipophilicity, solubility, and membrane permeation), were determined.
References
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Journal ArticleDOI
An improved catalytic OsO4 oxidation of olefins to cis-1,2-glycols using tertiary amine oxides as the oxidant
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On stereochemistry of osmium tetraoxide oxidation of allylic alcohol systems. Empirical rule
TL;DR: In this article, an empirical formulation is presented to predict the stereochemistry of major osmylation products of allylic alcohols and their derivatives, and an empirical model is proposed to predict their stereochemistry.
Journal ArticleDOI
The Polar Hydrophobicity of Fluorinated Compounds
TL;DR: Improved oral bioavailability is seen in some systems where fluorine substitution leads to improved hydrolytic stability and mechanism-based inhibitors for a wide variety of diseases and to chemotherapeutic drugs.
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Phosphotyrosyl mimetics in the development of signal transduction inhibitors.
Terrence R. Burke,Kyeong Lee +1 more
TL;DR: A perspective on the roles of pTyr residues in signal transduction and approaches to pT Tyr mimetic development is provided.