Abstract
Publisher Summary This chapter provides an overview of the synthesis of branched-chain sugars. The naturally occurring, branched-chain sugars were classified as rare sugars until the 1960's, but the discovery of numerous new sugars as the glycosidic component of antibiotics during the past two decades has stimulated extensive research on their chemistry and biochemistry. Most of the branched sugars found in Nature have a polar substituent at the branching carbon-atom (Type A); tertiary alcohols are commonest, but some of them are in the form of a methyl ether, acetate, or cyclic carbonate and, in several instances, an amino or a nitro group is attached to the tertiary carbon atom. Diversity is observed in the branchings, but some of them are chemically interconvertible and also can be derived from a common intermediate. This chapter explains the concepts related to the nucleophilic reactions of sugar oxiranes, aldol addition, and cyclization of dialdehydes with nitroalkanes. It also presents a brief discussion on methyl-branched sugars and two-carbon-branched sugar.
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