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Solvent-dependent, kinetically controlled stereoselective synthesis of 3- and 4- thioglycosides
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
2005 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 70, no 17, 6952-6955 p.Article in journal (Refereed) Published
Abstract [en]

Facile approaches to prepare 3- and 4-thioglycosides of the galacto, gulo, and gluco type from the parent triflates are presented. The dependencies of the solvent and the protecting group pattern, as well as the configuration of the neighboring and leaving groups, have been studied for these reactions. The results clearly show that the efficient stereo-selective synthesis of methyl 3-thin-galactoside depends highly on the solvent and the nucleophile concentration.

Place, publisher, year, edition, pages
2005. Vol. 70, no 17, 6952-6955 p.
Keyword [en]
Derivatives, Solvents, Stereochemistry, Synthesis (chemical)
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-6395DOI: 10.1021/jo050650rISI: 000231183000054Scopus ID: 2-s2.0-23644434820OAI: oai:DiVA.org:kth-6395DiVA: diva2:11093
Note
QC 20100915Available from: 2006-11-22 Created: 2006-11-22 Last updated: 2017-12-14Bibliographically approved
In thesis
1. Efficient carbohydrate synthesis by controlled inversion strategies
Open this publication in new window or tab >>Efficient carbohydrate synthesis by controlled inversion strategies
2006 (English)Licentiate thesis, comprehensive summary (Other scientific)
Abstract [en]

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.
Series
Trita-IOK, ISSN 1100-7974 ; 107
Keyword
Carbohydrate Chemistry, Carbohydrate Protection, Epimerization, Inversion, Dynamic, Regioselective Control, Neighboring Group Participation
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-4179 (URN)91-7178-502-7 (ISBN)
Presentation
2006-11-30, E2, KTH, Lindstedtsvägen 3, Stockholm, 10:00
Supervisors
Note
QC 20101111Available from: 2006-11-22 Created: 2006-11-22 Last updated: 2010-11-11Bibliographically approved
2. Carbohydrate Synthesis and Study of Carbohydrate-Lectin Interactions Using QCM Biosensors and Microarray Technologies
Open this publication in new window or tab >>Carbohydrate Synthesis and Study of Carbohydrate-Lectin Interactions Using QCM Biosensors and Microarray Technologies
2006 (English)Doctoral thesis, comprehensive summary (Other scientific)
Abstract [en]

Interactions between carbohydrates and proteins are increasingly being recognized as crucial in many biological processes, such as cellular adhesion and communication. In order to investigate the interactions of carbohydrates and proteins, the development of efficient analytic technologies, as well as novel strategies for the synthesis of carbohydrates, have to be explored. To date, several methods have been exploited to analyze interactions of carbohydrates and proteins, for example, biosensors, nuclear magnetic resonance (NMR); enzyme-linked immunosorbent assays (ELISA), X-ray crystallography and array technologies. This thesis describes the development of novel strategies for the synthesis of carbohydrates, as well as new efficient strategies to Quartz Crystal Microbalance- (QCM-) biosensors and carbohydrate microarrays technologies. These methodologies have been used to probe carbohydrate-lectin-interactions for a range of plant and animal lectins.

Place, publisher, year, edition, pages
Stockholm: KTH, 2006. 106 p.
Series
Trita-IOK, ISSN 1100-7974 ; 2006:106
Keyword
Lectins; Carbohydrates; Molecular recognition; Biosensors; Quartz crystal microbalance; Carbohydrate microarrays.
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-4177 (URN)91-7178-503-5 (ISBN)
Public defence
2006-12-01, D3, Lindstedtsvägen 5, Stockholm, 10:00
Opponent
Supervisors
Note
QC 20100915Available from: 2006-11-22 Created: 2006-11-22 Last updated: 2011-09-05Bibliographically approved

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