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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Contemporary Syntheses of 2-Ketoheptoses and Derivatives

Author(s): Anna Jacobsen and Joachim Thiem

Volume 18, Issue 22, 2014

Page: [2833 - 2841] Pages: 9

DOI: 10.2174/1385272819666141016215205

Price: $65

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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