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Total Synthesis of Trisaccharide Repeating Unit of Staphylococcus aureus Type 8 (CP8) Capsular Polysaccharide.

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Herein, we report a highly efficient total synthesis of Staphylococcus aureus type 8 trisaccharide repeating unit in a lesser number of steps and high stereoselectivity. The complex trisaccharide contains rare… Click to show full abstract

Herein, we report a highly efficient total synthesis of Staphylococcus aureus type 8 trisaccharide repeating unit in a lesser number of steps and high stereoselectivity. The complex trisaccharide contains rare amino sugars, viz., d-fucosamine, l-fucosamine, and 2-acetamido d-mannuronic acid. The installation of consecutive sterically hindered 1,2-cis glycosidic linkages, especially β-mannosylation, is the key challenge in this synthesis. The total synthesis of target molecule was completed via a longest linear sequence of 18 steps in 7.1% overall yield.

Keywords: trisaccharide repeating; aureus type; synthesis; staphylococcus aureus; repeating unit; total synthesis

Journal Title: Organic letters
Year Published: 2023

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