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De Novo Asymmetric Synthesis of Anthrax Tetrasaccharide and Related Tetrasaccharide

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Haibing Guo and George A. O’Doherty

Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506

J. Org. Chem., 2008, 73 (14), pp 5211–5220

DOI: 10.1021/jo800691v

Publication Date (Web): June 19, 2008

Abstract

A de novo asymmetric approach to the natural product anthrax tetrasaccharide 1 and an analogue 2 with an anomeric hexyl azide group has been developed from acetylfuran. The construction of the tetrasaccharide was achieved by a traditional [3 + 1] glycosylation strategy. An iterative diastereoselective palladium-catalyzed glycosylation, Luche reduction, diastereoselective dihydroxylation, and regioselective acylation were employed for the assembly of the l-rhamno-trisaccharide building block. The anthrose building block also required a palladium-catalyzed azide allylation and a triflate inversion to set the gluco-stereochemistry in addition to Luche reduction and dihydroxylation.

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Published In Issue July 18, 2008
Article ASAPJune 19, 2008
Received: March 27, 2008

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De Novo Asymmetric Synthesis of Anthrax Tetrasaccharide and Related Tetrasaccharide

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Recommend & Share

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