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Supramolecular Control in Carbohydrate Epimerization: Discovery of a New Anion Host−Guest System
KTH, Skolan för kemivetenskap (CHE), Kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi.ORCID-id: 0000-0003-2673-075X
KTH, Skolan för kemivetenskap (CHE), Kemi.
2008 (engelsk)Inngår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 130, s. 15270-15271Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
2008. Vol. 130, s. 15270-15271
Emneord [en]
MOLECULAR RECOGNITION; AROMATIC INTERACTIONS; ACTIVATION; INVERSION; COMPLEXES; CHEMISTRY; NITRITE
HSV kategori
Identifikatorer
URN: urn:nbn:se:kth:diva-9884DOI: 10.1021/ja807044pISI: 000263311300025Scopus ID: 2-s2.0-56449123629OAI: oai:DiVA.org:kth-9884DiVA, id: diva2:139844
Merknad
QC 20100709Tilgjengelig fra: 2009-01-27 Laget: 2009-01-27 Sist oppdatert: 2017-12-14bibliografisk kontrollert
Inngår i avhandling
1. Efficient Carbohydrate Synthesis By Intra- and Supramolecular Control
Åpne denne publikasjonen i ny fane eller vindu >>Efficient Carbohydrate Synthesis By Intra- and Supramolecular Control
2009 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
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.

sted, utgiver, år, opplag, sider
Stockholm: KTH, 2009. s. 59
Serie
Trita-CHE-Report, ISSN 1654-1081 ; 2009:2
Emneord
Carbohydrate Chemistry, Supramolecular Control, Ambident Reactivity
HSV kategori
Identifikatorer
urn:nbn:se:kth:diva-9882 (URN)978-91-7415-207-4 (ISBN)
Disputas
2009-02-05, F3, KTH, Lindstedtsvägen 26, Stockholm, 10:00 (engelsk)
Opponent
Veileder
Merknad
QC 20100709Tilgjengelig fra: 2009-01-27 Laget: 2009-01-26 Sist oppdatert: 2012-02-23bibliografisk kontrollert

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