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Contemporary Syntheses of 2-Ketoheptoses and Derivatives

[ Vol. 18 , Issue. 22 ]

Author(s):

Anna Jacobsen and Joachim Thiem   Pages 2833 - 2841 ( 9 )

Abstract:


Ketoheptoses are rarely found in Nature, yet early on D-manno-heptulose could be isolated from Avocado. Following detection of D-manno-heptulose to act as an inhibitor of glucokinase the involvement of ketoheptoses in biomedical applications required synthetic approaches. This review focuses on syntheses of ketoheptoses by rearrangement reactions (de Bruyn-van Ekenstein, Amadori, Bilik) as well as chain elongation reactions (Henry, Grignard, exocyclic enolethers) and gives an overview of the synthetic activity from early syntheses to most recent improvements.

Keywords:

2-ketoheptoses, chain elongation reactions, D-manno-heptulose, fluoro-deoxy-and amino-deoxy derivatives, non-invasive imaging, rearrangement reactions, synthesis of ketoheptoses, β-cells.

Affiliation:

University of Hamburg, Faculty of Science, Department of Chemistry, Martin-Luther-King-Pltz 6, D-20146 Hamburg, Germany.

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