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Evaluation of Thioglycosides of Kdo as Glycosyl Donor
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2007 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 342, no 3-4, 631-637 p.Article in journal (Refereed) Published
Abstract [en]

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 β-anomeric selectivity. The use of diethyl ether as solvent and (especially) isopropylidene acetals as protecting groups improved the α-anomeric selectivity. NIS/AgOTf as promoter surprisingly yielded the 3-iodo-product via the glycal intermediate.

Place, publisher, year, edition, pages
Elsevier , 2007. Vol. 342, no 3-4, 631-637 p.
Keyword [en]
Thioglycoside donors; Kdo glycosides; Thiophilic promoters
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-25824DOI: 10.1016/j.carres.2006.08.021ISI: 000244548700028OAI: oai:DiVA.org:su-25824DiVA: diva2:200604
Note
Part of urn:nbn:se:su:diva-894Available from: 2006-03-09 Created: 2006-03-09 Last updated: 2010-10-04Bibliographically approved
In thesis
1. Synthesis of Oligosaccharides from the Inner Core Structure of Haemophilus Influenzae and Neisseria meningitidis Lipopolysaccharides
Open this publication in new window or tab >>Synthesis of Oligosaccharides from the Inner Core Structure of Haemophilus Influenzae and Neisseria meningitidis Lipopolysaccharides
2006 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis describes the synthesis of oligosaccharides corresponding to different parts of the lipopolysaccharide (LPS) inner core structure from Haemophilus influenzae and Neisseria meningitidis. Chapter 2 describes the synthesis of a protected trisaccharide common to H. influenzae and N. meningitidis LPS, which can be used as a versatile precursor in further syntheses of larger LPS structures. In Chapter 3 syntheses towards phosphoethanolamine substituted trisaccharides corresponding to H. influenzae and N. meningitidis structures are presented. In Chapter 4 the synthesis of a H. influenzae tetrasaccharide structure, with and without a phosphoethanolamine substituent in the 6-position of the second heptose unit, is described. Conjugation to biotin of these two tetrasaccharides is also performed. Chapter 5 describes the synthesis of a spacer-equipped Kdo acceptor that is subsequently attached to the tetrasaccharide described in Chapter 4 forming a pentasaccharide from the inner core structure of H. influenzae. Similar to the synthesis of the tetrasaccharide, a phosphoethanolamine is attached to the 6 position of the second heptose. Chapter 5 also describes the synthesis of various Kdo thioglycoside donors and their evaluation in glycosylation reactions using different promoters and reaction conditions.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi, 2006
Keyword
Carbohydrate, synthesis, Haemophilus influenzae, Neisseria meningitidis
National Category
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-894 (URN)91-7155-217-0 (ISBN)
Public defence
2006-03-31, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 10:00
Opponent
Supervisors
Available from: 2006-03-09 Created: 2006-03-09Bibliographically approved

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