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Total Synthesis of the Repeating Unit of Streptococcus pneumoniae Zwitterionic Polysaccharide Sp1
Antara Ghosh1, Suvarn S Kulkarni1
1Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400076, India.
Abstract:
Reported herein is the total synthesis of the trisaccharide repeating unit of Streptococcus pneumoniae zwitterionic polysaccharide Sp1 containing a rare sugar, 2-acetamido-4-amino-2,4,6-trideoxy-d-galactose (AAT), and three consecutive 1,2-cis-glycosidic linkages. The total synthesis was completed via highly stereoselective glycosylations and late-stage oxidation as key steps involving a longest linear sequence of 21 steps with 4.4% overall yield.
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