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Synthetic routes toward pentasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O181

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Abstract An efficient synthetic strategy has been developed for the synthesis of the pentasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O181. A one-pot, two step iterative glycosylation… Click to show full abstract

Abstract An efficient synthetic strategy has been developed for the synthesis of the pentasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O181. A one-pot, two step iterative glycosylation and [2 + 3] block glycosylation strategy have been adopted for the construction of the pentasaccharide derivative 2, which was then transformed into target compound 1 after a series of functional group transformations. Here H2SO4-silica has been used successfully as a promoter for all glycosylation reaction. The stereoselective outcomes of all glycosylation reactions were very good. The 2-acetamido-2,6-dideoxy- l -glucose ( l -QuipNAc) building block was obtained from known carbohydrate l -rhamnose precursors.

Keywords: pentasaccharide repeating; repeating unit; antigen escherichia; unit corresponding; escherichia coli; corresponding antigen

Journal Title: Tetrahedron Letters
Year Published: 2019

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