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Abstract <p>Starting from (2-methyl-5-<i>tert-</i>butylphenyl)-2,3-di-<i>O</i>-benzyl-1-thio-β-d-glucopyranoside and phenyl-2-azido-3,4-di-<i>O</i>-acetyl-2-deoxy-1-seleno-α-l-fucopyranoside the (2-methyl-5-<i>tert-</i>butylphenyl)-4-<i>O</i>-(2-azido-3,4-di-<i>O</i>-acetyl-2-deoxy-α-l-fucopyranosyl)-2,3-di-<i>O</i>-benzyl-1-thio-β-d-glucopyranoside was synthesized, which is planned for the use in the assembly of oligosaccharides structurally related to the repeating unit of the <i>R. typhi O</i>-polysaccharide. During this work, the conditions for selective activation selenoglycoside in the glycosylation reaction were selected. It was also shown that the use of MeOTf as a promoter afford chemoselective activation of selenoglycoside in the presence of thioglycoside.</p>

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Synthesis of a Disaccharide Glycosyl Donor for Use in the Assembly of Oligosaccharides Structurally Related to the Repeating Unit of the Main Chain of Rickettsia typhi O-Polysaccharide

  • 期刊论文

  • 发表日期：

    2026年3月3日

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  • Timur M. Volkov,
  • Dmitry V. Yashunsky,
  • Nikolay E. Nifantiev

摘要

Abstract

Starting from (2-methyl-5-tert-butylphenyl)-2,3-di-O-benzyl-1-thio-β-d-glucopyranoside and phenyl-2-azido-3,4-di-O-acetyl-2-deoxy-1-seleno-α-l-fucopyranoside the (2-methyl-5-tert-butylphenyl)-4-O-(2-azido-3,4-di-O-acetyl-2-deoxy-α-l-fucopyranosyl)-2,3-di-O-benzyl-1-thio-β-d-glucopyranoside was synthesized, which is planned for the use in the assembly of oligosaccharides structurally related to the repeating unit of the R. typhi O-polysaccharide. During this work, the conditions for selective activation selenoglycoside in the glycosylation reaction were selected. It was also shown that the use of MeOTf as a promoter afford chemoselective activation of selenoglycoside in the presence of thioglycoside.