Fluorine-directed glycosylation.

Trichloroacetimidates of 2-fluoro substituted furanoses are investigated as glycosyl donors.

[1]  A. Slawin,et al.  Fluorosugars: synthesis of the 2,3,4-trideoxy-2,3,4-trifluoro hexose analogues of D-glucose and D-altrose and assessment of their erythrocyte transmembrane transport. , 2010, Chemical communications.

[2]  D. Crich Mechanism of a chemical glycosylation reaction. , 2010, Accounts of chemical research.

[3]  A. Demchenko,et al.  Mechanism of chemical O-glycosylation: from early studies to recent discoveries. , 2010, Organic & biomolecular chemistry.

[4]  K. Woerpel,et al.  Correlations between nucleophilicities and selectivities in the substitutions of tetrahydropyran acetals. , 2009, The Journal of organic chemistry.

[5]  T. Lowary,et al.  Recent advances in the synthesis of 2-deoxy-glycosides. , 2009, Carbohydrate research.

[6]  N. Sibson,et al.  Potent Fluoro‐oligosaccharide Probes of Adhesion in Toxoplasmosis , 2009, Chembiochem : a European journal of chemical biology.

[7]  P. Seeberger,et al.  2009 Claude S. Hudson Award in Carbohydrate Chemistry. Carbohydrates: a frontier in medicinal chemistry. , 2009, Journal of medicinal chemistry.

[8]  Ryan Gilmour,et al.  Fluorinated quinine alkaloids: synthesis, X-ray structure analysis and antimalarial parasite chemotherapy. , 2009, Chemistry.

[9]  S. Withers,et al.  Non-Stick Sugars: Synthesis of Difluorosugar Fluorides as Potential Glycosidase Inactivators , 2009 .

[10]  P. Seeberger Chemical glycobiology: why now? , 2009, Nature chemical biology.

[11]  H. Senn,et al.  The fluorine-iminium ion gauche effect: proof of principle and application to asymmetric organocatalysis. , 2009, Angewandte Chemie.

[12]  R. R. Schmidt,et al.  Neue Prinzipien für die Bildung von glycosidischen Bindungen , 2009 .

[13]  R. Schmidt,et al.  New principles for glycoside-bond formation. , 2009, Angewandte Chemie.

[14]  K. Woerpel,et al.  The effect of electrostatic interactions on conformational equilibria of multiply substituted tetrahydropyran oxocarbenium ions. , 2009, The Journal of organic chemistry.

[15]  Lisheng Cai,et al.  Chemistry with [18F]Fluoride Ion , 2008 .

[16]  G. Hart,et al.  Special Problems in Glycosylation Reactions: 2‐Deoxy Sugars , 2008 .

[17]  David O'Hagan,et al.  Understanding organofluorine chemistry. An introduction to the C-F bond. , 2008, Chemical Society reviews.

[18]  M. Bols,et al.  Going to extremes: "super" armed glycosyl donors in glycosylation chemistry. , 2007, Chemistry.

[19]  A. Slawin,et al.  An ElectrostaticGauche Effect in -Fluoro- and -Hydroxy-N-ethylpyridinium Cations , 2007 .

[20]  D. Crich,et al.  4,6-O-benzylidene-directed beta-mannopyranosylation and alpha-glucopyranosylation: the 2-deoxy-2-fluoro and 3-deoxy-3-fluoro series of donors and the importance of the O2-C2-C3-O3 interaction. , 2007, The Journal of organic chemistry.

[21]  K. Woerpel,et al.  Electrostatic effects on the reactions of cyclohexanone oxocarbenium ions. , 2006, The Journal of organic chemistry.

[22]  A. Slawin,et al.  The intramolecular β-fluorine⋯ammonium interaction in 4- and 8-membered rings , 2006 .

[23]  K. Woerpel,et al.  Electrostatic interactions in cations and their importance in biology and chemistry. , 2006, Organic & biomolecular chemistry.

[24]  K. Woerpel,et al.  Stereoselective C-glycosylation reactions of ribose derivatives: electronic effects of five-membered ring oxocarbenium ions. , 2005, Journal of the American Chemical Society.

[25]  J. Snyder,et al.  3-Fluoropiperidines and N-methyl-3-fluoropiperidinium salts: the persistence of axial fluorine. , 2005, Chemistry.

[26]  J. Dunitz Organic Fluorine: Odd Man Out , 2004, Chembiochem : a European journal of chemical biology.

[27]  C. R. Briggs,et al.  The observation of a large gauche preference when 2-fluoroethylamine and 2-fluoroethanol become protonated. , 2004, Organic & biomolecular chemistry.

[28]  K. Woerpel,et al.  Stereochemistry of nucleophilic substitution reactions depending upon substituent: evidence for electrostatic stabilization of pseudoaxial conformers of oxocarbenium ions by heteroatom substituents. , 2003, Journal of the American Chemical Society.

[29]  W. Roush,et al.  2-Deoxy-2-iodo-β-glucopyranosyl Fluorides: Mild and Highly Stereoselective Glycosyl Donors for the Synthesis of 2-Deoxy-β-glycosides from β-Hydroxy Ketones , 2003 .

[30]  C. R. Briggs,et al.  The CF bond as a tool in the conformational control of amides , 2003 .

[31]  W. Roush,et al.  Concerning the origin of the high beta-selectivity of glycosidation reactions of 2-deoxy-2-iodo-glucopyranosyl trichloroacetimidates. , 2002, Organic letters.

[32]  Lankin Dc,et al.  The NH---FC dipole orientation effect for pendant exocyclic CH(2)F. , 2002 .

[33]  A. Bérces,et al.  Can the stereochemical outcome of glycosylation reactions be controlled by the conformational preferences of the glycosyl donor? , 2002, Carbohydrate research.

[34]  C. Bertozzi,et al.  Surface molecular recognition , 2001, Proceedings of the National Academy of Sciences of the United States of America.

[35]  B. Smart Fluorine substituent effects (on bioactivity) , 2001 .

[36]  K. Nicolaou,et al.  Abenteuer in der Kohlenhydratchemie: Synthesestrategien, Synthesemethoden, Moleküldesign und biologische Chemie , 2001 .

[37]  K. Nicolaou,et al.  Adventures in Carbohydrate Chemistry: New Synthetic Technologies, Chemical Synthesis, Molecular Design, and Chemical Biology A list of abbreviations can be found at the end of this article. Telemachos Charalambous was an inspiring teacher at the Pancyprian Gymnasium, Nicosia, Cyprus. , 2001, Angewandte Chemie.

[38]  Carolyn R. Bertozzi,et al.  Chemical Glycobiology , 2001, Science.

[39]  R. Franck,et al.  The synthesis of 2-deoxyglycosides : 1988-1999 , 2000 .

[40]  J. Snyder,et al.  The Unexpected Diaxial Orientation of cis-3,5-Difluoropiperidine in Water: A Potent CF- - -NH Charge-Dipole Effect , 2000 .

[41]  K. Woerpel,et al.  Stereochemical Reversal of Nucleophilic Substitution Reactions Depending upon Substituent: Reactions of Heteroatom-Substituted Six-Membered-Ring Oxocarbenium Ions through Pseudoaxial Conformers , 2000 .

[42]  J. Howard,et al.  The preferred conformation of N-β-fluoroethylamides. Observation of the fluorine amide gauche effect , 2000 .

[43]  M. Albert,et al.  SYNTHESIS OF (2-DEOXY-2-FLUORO-GLYCOSYL)AMINO-ACIDS , 1999 .

[44]  W. Roush,et al.  2-Deoxy-2-iodo- and 2-deoxy-2-bromo-alpha-glucopyranosyl trichloroacetimidates: highly reactive and stereoselective donors for the synthesis of 2-deoxy-beta-glycosides. , 1999, Organic letters.

[45]  W. Roush,et al.  A Highly Stereoselective Synthesis of 2-Deoxy-β-glycosides Using 2-Deoxy-2-iodo-glucopyranosyl Acetate Donors , 1999 .

[46]  W. Roush,et al.  Total Synthesis of Olivomycin A , 1999 .

[47]  D. Yeagley,et al.  Experimental and Theoretical Evidence of Through-Space Electrostatic Stabilization of the Incipient Oxocarbenium Ion by an Axially Oriented Electronegative Substituent During Glycopyranoside Acetolysis , 1997 .

[48]  W. Roush,et al.  Stereoselective synthesis of 2-deoxy-β-glycosides from glycal precursors. 2. Stereochemistry of glycosidation reactions of 2-thiophenyl- and 2-selenophenyl-α-d-gluco-pyranosyl donors , 1997 .

[49]  K. Briner,et al.  Studies on the Synthesis of Aureolic Acid Antibiotics: Acyloin Glycosidation Studies. , 1996, The Journal of organic chemistry.

[50]  R. Schmidt,et al.  Anomeric-oxygen activation for glycoside synthesis: the trichloroacetimidate method. , 1994, Advances in carbohydrate chemistry and biochemistry.

[51]  C. V. Boeckel,et al.  Synthesis of Modified Di- and Trisaccharide Fragments of N-Glycoproteins , 1993 .

[52]  K. Tatsuta,et al.  Recent progress in O-glycosylation methods and its application to natural products synthesis , 1993 .

[53]  J. Snyder,et al.  Protonated 3-fluoropiperidines: an unusual fluoro directing effect and a test for quantitative theories of solvation , 1993 .

[54]  R. Madsen,et al.  n-Pentenyl Glycosides in Organic Chemistry: A Contemporary Example of Serendipity , 1992 .

[55]  C. W. Andrews,et al.  Molecular mechanical investigations of the properties of oxocarbenium ions. 1. Parameter development , 1992 .

[56]  C. W. Andrews,et al.  Molecular mechanical investigations of the properties of oxocarbenium ions. 2. Application to glycoside hydrolysis , 1992 .

[57]  M. Paddon-Row,et al.  The importance of electrostatic effects in controlling π-facial stereoselectivity in nucleophilic additions to carbonyl compounds: an ab initio MO study of a prototype chelation model , 1991 .

[58]  J. Irwin,et al.  Stereoelectronic Aspects of the Anomeric Effect in Fluoromethylamine , 1990 .

[59]  M. Paddon-Row,et al.  Theoretical evidence in support of the Anh–Eisenstein electronic model in controlling π-facial stereoselectivity in nucleophilic additions to carbonyl compounds , 1990 .

[60]  S. Withers,et al.  Hydrogen bonding and specificity. Fluorodeoxy sugars as probes of hydrogen bonding in the glycogen phosphorylase-glucose complex. , 1986, Biochemistry.