Current Organic Chemistry - Volume 18, Issue 13, 2014

Methodologies for the synthesis of polyhydroxylated carbocyclic derivatives with medium (7- and 8-member) rings are reviewed. Polyhydroxylated carbocyclic derivatives with larger rings are practically unknown; only few examples can be found in the literature. This review is focused on the methods of preparation rather than on the size of cyclitols. Various types of compounds with medium carbocyclic rings are discussed. S Read More

Carbohydrates have been utilized as starting materials for the synthesis of pyranopyrans, which are important building blocks for the total synthesis of polyethers and other natural products. This review focuses on the synthesis of pyranopyrans from carbohydrates, with emphasis on the stereoselective functionalization of sugars and on the methods used to construct additional rings onto a carbohydrate template. Anhydr Read More

Carbapyranoses, i.e., pyranose derivatives whose ring oxygen has been replaced by a methylene group, are currently recognized as valuable carbohydrate mimetics. A plethora of methods are available for their preparation, and among them the radical cyclization of suitably functionalized carbohydrate derivatives has already positioned itself as a reliable synthetic method. The present review aims to give an overview of th Read More

This review provides a comprehensive compilation of available literature concerning the synthesis and applications of cyclic nitrones derived from sugars and hydroxyacids. The most important recent developments and concepts related to this topic are emphasized.

Recent advances in stereocontrolled Wittig olefination of sugars with stabilized and semi-stabilized phosphoranes are reviewed. Transformations of free and protected sugars for chain elongation at both reducing and terminal ends, and branched chain construction at the carbon atoms 2, 3 and 5 demonstrate the usefulness of this reaction in the preparation of a number of biologically active molecules and their precursors, starti Read More

This review describes the applications of carbohydrate-derived ligands in enantioselective transition metal catalysis since 2008 year. The areas of hydrogenation with molecular hydrogen and transfer hydrogenation, allylic substitution, 1,4-conjugate addition, epoxidation, cyclopropanation and addition to carbon-heteroatom double bonds are covered.

Chemical reactions using isomaltulose as the starting material leading to advanced functional carbohydrate derivatives are reviewed. A focus is made notably on the synthesis and application of different kinds of carboxylic acids and lactones obtained by oxidation of isomaltulose and the strategies using its triply dehydrated derivative, glycosyloxymethylfurfural.

The increased appreciation of the role of carbohydrates in the biological sciences has resulted in a multidisciplinary interest in carbohydrate chemistry. The widespread use of these materials is due to both their availability as well as the need for green and renewable bio-based materials. Moreover, sugar-containing synthetic polymers are being increasingly investigated as biodegradable, biocompatible and biorenewable Read More