Seven-Step Synthesis of All-Nitrogenated Sugar Derivatives Using Sequential Overman Rearrangements

Yuya Okuyama, Mayu Kidena, Erina Kato, Sayaka Kawano, Koki Ishii, Kenta Maie, Kazuki Miura, Siro Simizu, Takaaki Sato, Noritaka Chida

Research output: Contribution to journalArticlepeer-review

Abstract

All-nitrogenated sugars (ANSs), in which all hydroxy groups in a carbohydrate are replaced with amino groups, are anticipated to be privileged structures with useful biological activities. However, ANS synthesis has been challenging due to the difficulty in the installation of multi-amino groups. We report herein the development of a concise synthetic route to peracetylated ANSs in seven steps from commercially available monosaccharides. The key to success is the use of the sequential Overman rearrangement, which enables formal simultaneous substitution of four or five hydroxy groups in monosaccharides with amino groups. A variety of ANSs are available through the same reaction sequence starting from different initial monosaccharides by chirality transfer of secondary alcohols. Transformations of the resulting peracetylated ANSs such as glycosylation and deacetylation are also demonstrated. Biological studies reveal that ANS-modified cholesterol show cytotoxicity against human cancer cell lines, whereas each ANS and cholesterol have no cytotoxicity.

Original languageEnglish
Pages (from-to)5193-5198
Number of pages6
JournalAngewandte Chemie - International Edition
Volume60
Issue number10
DOIs
Publication statusPublished - 2021 Mar 1

Keywords

  • all-nitrogenated sugar
  • aminoglycosides
  • domino reaction
  • iminosugar
  • sigmatropic rearrangement

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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