Contemporary Syntheses of 2-Ketoheptoses and Derivatives

Author(s): Anna Jacobsen, Joachim Thiem

Journal Name: Current Organic Chemistry

Volume 18 , Issue 22 , 2014


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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.

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Article Details

VOLUME: 18
ISSUE: 22
Year: 2014
Published on: 26 November, 2014
Page: [2833 - 2841]
Pages: 9
DOI: 10.2174/1385272819666141016215205
Price: $58

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