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5: Acetals & Ethers

  • Page ID
    24021

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    I. Introduction

    Acetals are pervasive in carbo­hy­drate chemistry. They link together sac­cha­ride units in oligo- and polysac­cha­r­ides, provide the bonding in glycosides that joins carbohydrate and aglycon por­tions of a molecule, and furnish protection for hydroxyl groups during synthetic transformations. Because acetals have these vital protective and connective roles, their stability in the presence of free radicals is critical in enabling radical reactions selectively to modify other parts of a carbo­hy­drate structure. Even though most acetals are stable in the presence of the carbon-centered radi­cals typically encountered in carbohydrate chemistry, there are reac­tions between hetero­atom-cen­tered radicals and acetals that are useful in carbo­hydrate transformation.

    Ethers also serve as hydroxyl protecting groups during carbohydrate synthesis because, like acetals, they are unreactive in the presence of most carbon-centered radicals. When reaction of an ether or acetal does occur, it typically is hydrogen-atom abstraction from a carbon atom that has an attached oxygen atom.


    This page titled 5: Acetals & Ethers is shared under a All Rights Reserved (used with permission) license and was authored, remixed, and/or curated by Roger W. Binkley and Edith R. Binkley.

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