Literature DB >> 17027943

Evaluation of thioglycosides of Kdo as glycosyl donors.

Karin Mannerstedt1, Kerstin Ekelöf, Stefan Oscarson.   

Abstract

The use of Kdo thioglycosides as glycosyl donors using DMTST, IBr/AgOTf and NIS/AgOTf as promoters has been evaluated. Activation at low temperature allowed to escape the formation of 2,3-glycal byproducts to give glycosides in high yield and with good beta-anomeric selectivity. The use of diethyl ether as solvent and (especially) isopropylidene acetals as protecting groups improved the alpha-anomeric selectivity. NIS/AgOTf as promoter surprisingly yielded the 3-iodo-product via the glycal intermediate.

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Year:  2006        PMID： 17027943     DOI： 10.1016/j.carres.2006.08.021

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN： 0008-6215            Impact factor:   2.104


  8 in total

1.  Stereocontrolled Synthesis of the Equatorial Glycosides of 3-Deoxy-d-manno-oct-2-ulosonic Acid: Role of Side Chain Conformation.

Authors:  Philemon Ngoje; David Crich
Journal:  J Am Chem Soc       Date:  2020-04-14       Impact factor: 15.419

2.  Biochemical Characterization of Bifunctional 3-Deoxy-β-d-manno-oct-2-ulosonic Acid (β-Kdo) Transferase KpsC from Escherichia coli Involved in Capsule Biosynthesis.

Authors:  Olga G Ovchinnikova; Liam Doyle; Bo-Shun Huang; Matthew S Kimber; Todd L Lowary; Chris Whitfield
Journal:  J Biol Chem       Date:  2016-08-17       Impact factor: 5.157

3.  Stereoselective Synthesis of 5-epi-α-Sialosides Related to the Pseudaminic Acid Glycosides. Reassessment of the Stereoselectivity of the 5-Azido-5-deacetamidosialyl Thioglycosides and Use of Triflate as Nucleophile in the Zbiral Deamination of Sialic Acids.

Authors:  Bibek Dhakal; Szymon Buda; David Crich
Journal:  J Org Chem       Date:  2016-11-10       Impact factor: 4.354

4.  Progress in Kdo-glycoside chemistry.

Authors:  Paul Kosma
Journal:  Tetrahedron Lett       Date:  2016-05-18       Impact factor: 2.415

5.  Synthesis of chlamydia lipopolysaccharide haptens through the use of α-specific 3-iodo-Kdo fluoride glycosyl donors.

Authors:  Barbara Pokorny; Paul Kosma
Journal:  Chemistry       Date:  2014-10-29       Impact factor: 5.236

6.  Scope and Limitations of 3-Iodo-Kdo Fluoride-Based Glycosylation Chemistry using N-Acetyl Glucosamine Acceptors.

Authors:  Barbara Pokorny; Paul Kosma
Journal:  ChemistryOpen       Date:  2015-07-29       Impact factor: 2.911

7.  Synthesis of Neoglycoconjugates Containing 4-Amino-4-deoxy-l-arabinose Epitopes Corresponding to the Inner Core of Burkholderia and Proteus Lipopolysaccharides.

Authors:  Markus Blaukopf; Bernhard Müller; Andreas Hofinger; Paul Kosma
Journal:  European J Org Chem       Date:  2011-11-16

8.  Glycosyl dithiocarbamates: β-selective couplings without auxiliary groups.

Authors:  Panuwat Padungros; Laura Alberch; Alexander Wei
Journal:  J Org Chem       Date:  2014-02-27       Impact factor: 4.354
  8 in total

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