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Supramolecular Control in Carbohydrate Epimerization: Discovery of a New Anion Host−Guest System
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.ORCID iD: 0000-0003-2673-075X
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
2008 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 130, 15270-15271 p.Article in journal (Refereed) Published
Abstract [en]

A new anion-carbohydrate recognition system is described. Pyranosides with axial protons in 1-, 3-, and 5-position proved efficient, forming relatively strong complexes between the anion and the B-face of the carbohydrate. This system could furthermore be used in supramolecular control in Lattrell-Dax epimerization reactions, leading to either activation or deactivation effects.

Place, publisher, year, edition, pages
2008. Vol. 130, 15270-15271 p.
Keyword [en]
MOLECULAR RECOGNITION; AROMATIC INTERACTIONS; ACTIVATION; INVERSION; COMPLEXES; CHEMISTRY; NITRITE
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-9884DOI: 10.1021/ja807044pISI: 000263311300025Scopus ID: 2-s2.0-56449123629OAI: oai:DiVA.org:kth-9884DiVA: diva2:139844
Note
QC 20100709Available from: 2009-01-27 Created: 2009-01-27 Last updated: 2017-12-14Bibliographically approved
In thesis
1. Efficient Carbohydrate Synthesis By Intra- and Supramolecular Control
Open this publication in new window or tab >>Efficient Carbohydrate Synthesis By Intra- and Supramolecular Control
2009 (English)Doctoral thesis, comprehensive summary (Other academic)
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, the effects of the neighboring group on the Lattrell-Dax inversion were explored. A new carbohydrate/anion host-guest system was discovered and the ambident reactivity of the nitrite anion was found to cause a complicated behavior of the reaction. It has been demonstrated that a neighboring equatorial ester group plays a highly important role in this carbohydrate epimerization reaction, restricting the nitrite N-attack, thus resulting in O-attack only and 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 double parallel and double serial inversion. A supramolecularly activated, triggered cascade reaction was also developed. This cascade reaction is triggered by a deprotonation process that is activated by anions. It was found that the anions can activate this reaction following their hydrogen bonding tendencies to the hydroxyl group in aprotic solvents.

Place, publisher, year, edition, pages
Stockholm: KTH, 2009. 59 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2009:2
Keyword
Carbohydrate Chemistry, Supramolecular Control, Ambident Reactivity
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-9882 (URN)978-91-7415-207-4 (ISBN)
Public defence
2009-02-05, F3, KTH, Lindstedtsvägen 26, Stockholm, 10:00 (English)
Opponent
Supervisors
Note
QC 20100709Available from: 2009-01-27 Created: 2009-01-26 Last updated: 2012-02-23Bibliographically approved

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Publisher's full textScopushttp://pubs.acs.org/doi/abs/10.1021/ja807044p

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Brinck, Tore

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