title: De novo asymmetric synthesis of the pyranoses: from monosaccharides to oligosaccharides.
abstract: The various methods for the de novo asymmetric synthesis of the pyranose sugars are surveyed. The presentation begins with the work of Masamune and Sharpless with the use of the Sharpless asymmetric epoxidation for the synthesis of all eight l-hexoses. The development of other asymmetric reactions and their application for the synthesis of specific hexopyranoses are further discussed. The broad application of the Achmatowicz rearrangement with asymmetric catalysis, for the synthesis of various pyranones and imino sugars, is also presented. Finally, the use of a diastereoselective palladium-catalyzed glycosylation with the Achmatowicz approach for the synthesis of oligosaccharides and applications to medicinal chemistry are discussed.
authors.affiliation: Department of Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts, USA.
authors.forename: Alhanouf Z
authors.initials: AZ
authors.lastname: Aljahdali
authors.forename: Pei
authors.initials: P
authors.lastname: Shi
authors.forename: Yashan
authors.initials: Y
authors.lastname: Zhong
authors.forename: George A
authors.initials: GA
authors.lastname: O'Doherty
mesh_terms: D055162:Biocatalysis; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D006801:Humans; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009844:Oligosaccharides / Q000737:chemistry*; D010084:Oxidation-Reduction; D011714:Pyrans / Q000737:chemistry*
chemical_list: D009005:Monosaccharides; D009844:Oligosaccharides; D011714:Pyrans
keywords: Carbohydrate synthesis; De novo synthesis; Medicinal chemistry; Oligosaccharide de novo synthesis; Palladium-catalyzed glycosylation