Add time:07/18/2019         Source:sciencedirect.com

Publisher SummaryThis chapter provides an overview of the chemistry of anhydro sugars. Anhydro sugars, also called “intramolecular anhydrides,” are heteromorphic sugar derivatives that formally arise by the elimination of one or more water molecules from arbitrary hydroxyl groups of the parent aldose or ketose. They usually contain a bicyclic or tricyclic skeleton composed of oxirane, oxetane, oxolane (tetrahydrofuran), and oxane (tetrahydropyran) rings. If the hemiacetal group is involved in the formation of such a ring, the resulting glycose anhydride exhibits properties approaching ordinary glycosides. In general, the reactivity of anhydro sugars is determined mostly by the size of the oxygen rings. Oxirane and oxetane rings show a high reactivity, whereas oxolane and oxane rings are less reactive. However, the position of the anhydro bond, the steric arrangement, and the conformation of the molecule also play a significant role. Nowadays, anhydro sugars constitute very versatile starting materials not only in carbohydrate chemistry but also for the synthesis of noncarbohydrate and nonnatural compounds. In the past two decades, the interest in anhydro sugars has increased because they have been shown to be suitable monomers for preparing stereoregular polysaccharides and their specifically substituted derivatives.

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