We report the first total synthesis of conjugation-ready trisaccharide repeating units from Acinetobacter baumannii clinical isolates MG1 and strain 24, both featuring the same trisaccharide framework. A key synthetic challenge addressed here is the stereoselective installation of a 1,2-cis glycosidic linkage with a poorly nucleophilic axially oriented C4-OH of the d-GalNAcA acceptor, which was efficiently achieved by conformational switching of the pyranose ring from 4C1 to 1C4 leading to enhanced reactivity.
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Aishwarya Shelke
Kartikey Singh
Suvarn S. Kulkarni
Organic Letters
Indian Institute of Technology Bombay
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Shelke et al. (Mon,) studied this question.
www.synapsesocial.com/papers/69df2c62e4eeef8a2a6b171e — DOI: https://doi.org/10.1021/acs.orglett.6c01063
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