Synthesis of the Hexasaccharide Fragment of Landomycin A: Application of Glycosyl Tetrazoles and Phosphites in the Synthesis of a Deoxyoligosaccharide

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Abstract

The synthesis of the hexasaccharide fragment of the antitumor antibiotic landomycin A (1) (aka. NSC 639187) is described. The stereocontrolled introduction of key glycoside linkages relies on the combined application of glycosyl tetrazoles and phosphites to establish α and β glycosidic linkages, respectively. Spectral comparison of landomycin A octaacetate (2) and hexasaccharide pentaacetate (3) serves to corroborate the assigned structure of 1 within the oligosaccharide domain.

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