Total Synthesis of a Linear Tetrasaccharide Repeating Unit of MO6-24.

Org Lett

Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.

Published: October 2023

AI Article Synopsis

  • This study presents the complete synthesis of a specific tetrasaccharide unit found in MO6-24, which includes uncommon amino sugars.
  • *The synthesis involved overcoming challenges like creating rare deoxy amino sugars, forming consecutive glycosidic linkages, and performing late-stage oxidation.
  • *The entire process was achieved in 29 steps, starting from l-rhamnose, resulting in a low overall yield of 0.7%.

Article Abstract

Herein, we report the total synthesis of a linear, conjugation-ready, tetrasaccharide repeating unit of MO6-24, which is composed of rare amino sugars such as l-quinovosamine and d-galactosamine uronic acid. The key challenges addressed here are the synthesis of rare deoxy amino sugars, installation of consecutive 1,2- glycosidic linkages, and late-stage oxidation. Total synthesis of the target molecule was completed via a longest linear sequence of 29 steps in an overall yield of 0.7% starting from l-rhamnose.

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http://dx.doi.org/10.1021/acs.orglett.3c02872DOI Listing

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