Literature DB >> 17017782

Stereocontrolled synthesis of beta-D-mannuronic acid esters: synthesis of an alginate trisaccharide.

Leendert J van den Bos1, Jasper Dinkelaar, Herman S Overkleeft, Gijsbert A van der Marel.   

Abstract

A facile synthesis route toward beta-linked mannuronic acid oligomers using the corresponding 1-thiomannuronic acid esters in combination with the Ph2SO/Tf2O or NIS/TMSOTf reagent combinations is presented. The presence of the remotely attached carboxylic ester sufficiently influences the electronic environment to allow good to excellent beta-selectivities.

Entities:  

Year:  2006        PMID： 17017782     DOI： 10.1021/ja064787q

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  7 in total

Review 1.  Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Authors:  Matteo Panza; Salvatore G Pistorio; Keith J Stine; Alexei V Demchenko
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

2.  Automated fluorous-assisted solution-phase synthesis of β-1,2-, 1,3-, and 1,6-mannan oligomers.

Authors:  Shu-Lun Tang; Nicola L B Pohl
Journal:  Carbohydr Res       Date:  2016-04-06       Impact factor: 2.104

3.  A Mechanistic Probe into 1,2-cis Glycoside Formation Catalyzed by Phenanthroline and Further Expansion of Scope.

Authors:  Jiayi Li; Hien M Nguyen
Journal:  Adv Synth Catal       Date:  2021-07-05       Impact factor: 5.981

4.  The influence of acceptor nucleophilicity on the glycosylation reaction mechanism.

Authors:  S van der Vorm; T Hansen; H S Overkleeft; G A van der Marel; J D C Codée
Journal:  Chem Sci       Date:  2016-11-09       Impact factor: 9.825

5.  Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate.

Authors:  Eleni Dimitriou; Gavin J Miller
Journal:  Beilstein J Org Chem       Date:  2021-07-05       Impact factor: 2.883

6.  Automated Solution-Phase Synthesis of β-1,4-Mannuronate and β-1,4-Mannan.

Authors:  Shu-Lun Tang; Nicola L B Pohl
Journal:  Org Lett       Date:  2015-05-08       Impact factor: 6.005

7.  Automated Solution-Phase Synthesis of Insect Glycans to Probe the Binding Affinity of Pea Enation Mosaic Virus.

Authors:  Shu-Lun Tang; Lucas B Linz; Bryony C Bonning; Nicola L B Pohl
Journal:  J Org Chem       Date:  2015-10-12       Impact factor: 4.354
  7 in total

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