Literature DB >> 22592962

Fluorine-directed β-galactosylation: chemical glycosylation development by molecular editing.

Estelle Durantie1, Christoph Bucher, Ryan Gilmour.   

Abstract

Validation of the 2-fluoro substituent as an inert steering group to control chemical glycosylation is presented. A molecular editing study has revealed that the exceptional levels of diastereocontrol in glycosylation processes by using 2-fluoro-3,4,6-tri-O-benzyl glucopyranosyl trichloroacetimidate (TCA) scaffolds are a consequence of the 2R,3S,4S stereotriad. This study has also revealed that epimerization at C4, results in a substantial enhancement in β-selectivity (up to β/α 300:1).
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 22592962     DOI： 10.1002/chem.201200468

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  14 in total

1.  Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions.

Authors:  Yongho Park; Kaid C Harper; Nadine Kuhl; Eugene E Kwan; Richard Y Liu; Eric N Jacobsen
Journal:  Science       Date:  2017-01-13       Impact factor: 47.728

Review 2.  Recent Advances in Stereoselective Chemical O-Glycosylation Reactions.

Authors:  Mana Mohan Mukherjee; Rina Ghosh; John A Hanover
Journal:  Front Mol Biosci       Date:  2022-06-14

3.  Hyperconjugative Interactions of the Carbon-Halogen Bond that Influence the Geometry of Cyclic α-Haloacetals.

Authors:  Krystyna M Demkiw; Chunhua T Hu; K A Woerpel
Journal:  J Org Chem       Date:  2022-04-01       Impact factor: 4.198

4.  H12461. Fluorine as a Regiocontrol Element in the Ring Openings of Bicyclic Aziridiniums.

Authors:  Yu-Hong Lam; Kendall N Houk; Janine Cossy; Domingo Gomez Prado; Anne Cochi
Journal:  Helv Chim Acta       Date:  2012-11-19       Impact factor: 2.164

5.  Phenanthroline-Catalyzed Stereoretentive Glycosylations.

Authors:  Fei Yu; Jiayi Li; Paul M DeMent; Yi-Jung Tu; H Bernhard Schlegel; Hien M Nguyen
Journal:  Angew Chem Int Ed Engl       Date:  2019-04-09       Impact factor: 15.336

6.  TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals.

Authors:  Mei-Yuan Hsu; Yi-Pei Liu; Sarah Lam; Su-Ching Lin; Cheng-Chung Wang
Journal:  Beilstein J Org Chem       Date:  2016-08-04       Impact factor: 2.883

7.  Phenanthroline-Catalyzed Stereoselective Formation of α-1,2-cis 2-Deoxy-2-Fluoro Glycosides.

Authors:  Paul M DeMent; Chenlu Liu; Joseph Wakpal; Richard N Schaugaard; H Bernhard Schlegel; Hien M Nguyen
Journal:  ACS Catal       Date:  2021-02-02       Impact factor: 13.084

8.  Halogen-directed chemical sialylation: pseudo-stereodivergent access to marine ganglioside epitopes.

Authors:  Taiki Hayashi; Alexander Axer; Gerald Kehr; Klaus Bergander; Ryan Gilmour
Journal:  Chem Sci       Date:  2020-03-26       Impact factor: 9.825

9.  Introducing affinity and selectivity into galectin-targeting nanoparticles with fluorinated glycan ligands.

Authors:  Sarah-Jane Richards; Tessa Keenan; Jean-Baptiste Vendeville; David E Wheatley; Harriet Chidwick; Darshita Budhadev; Claire E Council; Claire S Webster; Helene Ledru; Alexander N Baker; Marc Walker; M Carmen Galan; Bruno Linclau; Martin A Fascione; Matthew I Gibson
Journal:  Chem Sci       Date:  2020-11-16       Impact factor: 9.825

10.  Influence of Configuration at the 4- and 6-Positions on the Conformation and Anomeric Reactivity and Selectivity of 7-Deoxyheptopyranosyl Donors: Discovery of a Highly Equatorially Selective l-glycero-d-gluco-Heptopyranosyl Donor.

Authors:  Kapil Upadhyaya; Rahul S Bagul; David Crich
Journal:  J Org Chem       Date:  2021-08-03       Impact factor: 4.198
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