Efficient carbohydrate synthesis by controlled inversion strategies
2006 (English)Licentiate thesis, comprehensive summary (Other scientific)
The Lattrell-Dax method of nitrite-mediated substitution of carbohydrate triflates is an efficient method to generate structures of inverse configuration. In this study it has been demonstrated that a neighboring equatorial ester group plays a highly important role in this carbohydrate epimerization reaction, inducing the formation of inversion compounds in good yields. Based on this effect, efficient synthetic routes to a range of carbohydrate structures, notably β-D-mannosides and β-D-talosides, were designed. By use of the ester activation effect for neighboring groups, a double parallel as well as a double serial inversion strategy was developed.
Place, publisher, year, edition, pages
Stockholm: KTH , 2006. , 40 p.
Trita-IOK, ISSN 1100-7974 ; 107
Carbohydrate Chemistry, Carbohydrate Protection, Epimerization, Inversion, Dynamic, Regioselective Control, Neighboring Group Participation
IdentifiersURN: urn:nbn:se:kth:diva-4179ISBN: 91-7178-502-7OAI: oai:DiVA.org:kth-4179DiVA: diva2:11097
2006-11-30, E2, KTH, Lindstedtsvägen 3, Stockholm, 10:00
QC 201011112006-11-222006-11-222010-11-11Bibliographically approved
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