Literature DB >> 15012078

Unique reactions of glycosyl iodides with oxa- and thiocycloalkane acceptors.

Darrin R Dabideen1, Jacquelyn Gervay-Hague.   

Abstract

[reaction: see text] Glucosyl-, galactosyl-, and mannosyl iodides efficiently react with strained oxacycloalkane acceptors to afford O-glycosides with high beta-selectivity. The mechanism of ring opening was investigated by reacting mannosyl iodides with pure enantiomers of propylene oxide and styrene oxide. Competition experiments between three- and five-membered oxacycloalkanes were also investigated. Finally, beta-thiomannosides were synthesized from thiocycloalkane acceptors.

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Year:  2004        PMID： 15012078     DOI： 10.1021/ol049966w

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

1.  Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.

Authors:  David Crich
Journal:  J Org Chem       Date:  2011-10-04       Impact factor: 4.354

2.  Two-step functionalization of oligosaccharides using glycosyl iodide and trimethylene oxide and its applications to multivalent glycoconjugates.

Authors:  Hsiao-Wu Hsieh; Ryan A Davis; Jessica A Hoch; Jacquelyn Gervay-Hague
Journal:  Chemistry       Date:  2014-04-08       Impact factor: 5.236

3.  Direct Experimental Characterization of a Bridged Bicyclic Glycosyl Dioxacarbenium Ion by 1 H and 13 C NMR Spectroscopy: Importance of Conformation on Participation by Distal Esters.

Authors:  Kapil Upadhyaya; Yagya P Subedi; David Crich
Journal:  Angew Chem Int Ed Engl       Date:  2021-10-21       Impact factor: 15.336

4.  Glycosylated cyclophellitol-derived activity-based probes and inhibitors for cellulases.

Authors:  Casper de Boer; Nicholas G S McGregor; Evert Peterse; Sybrin P Schröder; Bogdan I Florea; Jianbing Jiang; Jos Reijngoud; Arthur F J Ram; Gilles P van Wezel; Gijsbert A van der Marel; Jeroen D C Codée; Herman S Overkleeft; Gideon J Davies
Journal:  RSC Chem Biol       Date:  2020-07-28

Review 5.  Chemical O-Glycosylations: An Overview.

Authors:  Rituparna Das; Balaram Mukhopadhyay
Journal:  ChemistryOpen       Date:  2016-08-17       Impact factor: 2.911

Review 6.  Anomeric O-Functionalization of Carbohydrates for Chemical Conjugation to Vaccine Constructs.

Authors:  Simon S Park; Hsiao-Wu Hsieh; Jacquelyn Gervay-Hague
Journal:  Molecules       Date:  2018-07-17       Impact factor: 4.411
  6 in total

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