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Synthesis 2025; 57(20): 2969-2976
DOI: 10.1055/a-2642-4514
DOI: 10.1055/a-2642-4514
Paper
Straightforward Synthesis of Functionalized l-Quinovosamine Thioglycoside Derivatives and Their Direct Use in the Synthesis of the Tetrasaccharide Corresponding to the Cell Wall of Escherichia coli O98
Authors
Abstract
Synthesis of functionalized l-quinovosamine thioglycoside was achieved in very good yield using simple functional group manipulation of l-rhamnose. l-quinovosamine thioglycoside derivatives have been successfully used in the total synthesis of the tetrasaccharide repeating unit of the cell wall O-antigen of Escherichia coli O98 strain. Two units of l-quinovosamine thioglycoside were stereoselectively glycosylated during the synthesis of the tetrasaccharide. In addition, direct conversion of azido groups into acetamido functionality and TEMPO-mediated (diacetoxyiodo)benzene (DAIB) oxidation of a primary hydroxyl group to a carboxylic group are noteworthy features of the synthetic strategy.
Publication History
Received: 29 April 2025
Accepted after revision: 24 June 2025
Article published online:
08 August 2025
© 2025. Thieme. All rights reserved.
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