Carbocyclic Carbohydrate Mimics as Potential Glycosidase Inhibitors

Mette Fanefjord, Inge Lundt

Research output: Contribution to conferencePosterResearch

Abstract

It has been proven that aminocyclopentanols having the aminogroup adjacent to a carbon sidechain could be potential anomer-selective glycosidase inhibitors [1]. A successful pathway for synthesising mimics to L-carbohydrates 2, by introducing nitrogen to the C6 position in compound 1, has been developed in our group. A similar strategy has been used for synthesising mimics of D-carbohydrates. The α,β-unsaturated lactone 3 was cyclised to compound 4 which was further transformed into 5. The nitrogen functionality in compound 7 is introduced by an Overman rearrangement of 6 and the hydroxyl functionalities was introduced by either epoxidation or dihydroxylation of 7. Finally, reduction of the lactone ring led to the sugar mimics 8. The synthesis of several isomers of 8 will be presented. [1] a) Kleban, M. ; Hilgers, P. ; Greul, J.N. ; Kugler, R.D. ; Li, J. ; Picasso, S. ; Vogel, P. ; Jäger, V. ChemBioChem, 2001, 5, 365-368. b) Reymond, J-L. ; Leroy, E. Org. Lett. 1999, 5, 775-777. [2] Marie Lauritsen Ph.D. project.
Original languageEnglish
Publication date2004
Publication statusPublished - 2004
Event22nd International Carbohydrate Symposium - Glasgow, United Kingdom
Duration: 23 Jul 200427 Jul 2004
Conference number: 22

Conference

Conference22nd International Carbohydrate Symposium
Number22
CountryUnited Kingdom
CityGlasgow
Period23/07/200427/07/2004

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