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Improved Synthesis of 1,3,4,6-tetra-O-acetyl-2-Azido-2-deoxy-α-D-mannopyranose
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2005 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 340, no 17, 2675-2676 p.Article in journal (Refereed) Published
Abstract [en]

By improved (anhydrous) work-up conditions of a triflate displacement reaction, the yield in the preparation of the versatile synthetic intermediate 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-d-mannopyranose has been significantly enhanced. This important precursor is now available in three efficient steps from d-glucose.

Place, publisher, year, edition, pages
Elsevier Ltd , 2005. Vol. 340, no 17, 2675-2676 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-23909DOI: 10.1016/j.carres.2005.09.008OAI: oai:DiVA.org:su-23909DiVA: diva2:195285
Note
Part of urn:nbn:se:su:diva-545Available from: 2005-05-19 Created: 2005-05-19 Last updated: 2010-11-02Bibliographically approved
In thesis
1. Synthesis of oligosaccharides related to the capsular polysaccharide of Neisseria meningitidis serotype A
Open this publication in new window or tab >>Synthesis of oligosaccharides related to the capsular polysaccharide of Neisseria meningitidis serotype A
2005 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

In order to find suitable stable vaccine candidates against Neisseria meningitidis group A, several structures related to the capsular polysaccharide have been synthesised. The first part of the thesis describes the synthesis of C-phosphonate analogues starting from glucose. The key step is a Mitsunobu coupling of a methyl C-phosphonate monomer to the 6-hydroxyl group of a 2-acetamido mannose derivative. Contained within this work is a description of an improved synthesis of 2-azido-2-deoxy-D-mannopyranose. The second part outlines the synthesis of structural elements present in the native capsular polysaccharide of Neisseria meningitidis serotype A including different acetylation and phosphorylation patterns. The final chapter describes an improved synthesis of the Lewis b hexasaccharide needed for purification of and interaction studies with the Helicobacter pylori adhesin BabA.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi, 2005. 40 p.
National Category
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-545 (URN)91-7155-091-7 (ISBN)
Public defence
2005-06-10, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 10:00
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Available from: 2005-05-19 Created: 2005-05-19Bibliographically approved

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