Divergent synthesis of L-sugars and L-iminosugars from D-sugars

Hideyo Takahashi, Tomomi Shida, Yuko Hitomi, Yoshinori Iwai, Namisa Miyama, Kazusa Nishiyama, Daisuke Sawada, Shiro Ikegami

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15 Citations (Scopus)

Abstract

An efficient divergent synthesis of L-sugars and L-iminosugars from D-sugars is described. The important intermediate. δ-hydroxyalkoxamate. prepared from D-glucono-/galactono-1,5-lactone, was cyclized under Mitsunobu conditions to give the O-cyclized oxime compound and the N-cyclized lactam compound as mixtures. A more detailed investigation revealed that the appropriate protecting groups and solvents controlled the specificity for the O-/N-cyclization of the δ-hydroxyalkoxamate. Suitable protection at the 6-position of δ-hydroxyalkoxamate. derived from D-glucono-1,5-lactone, afforded the corresponding O-alkylation product alone. Thus we succeeded in applying this to the total synthesis of L-iduronic acid. In contrast, with both TBDMS as the protecting group and RCN as the solvent the efficient conversion of δ-glucono/galactono-1,5-lactone into the corresponding L-iminosugars (L-idonolactam and L-altronolactam) was achieved.

Original languageEnglish
Pages (from-to)5868-5877
Number of pages10
JournalChemistry - A European Journal
Volume12
Issue number22
DOIs
Publication statusPublished - Jul 24 2006

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Keywords

  • Azasugars
  • Carbohy-drates
  • Lactams
  • Lactones
  • Mitsunobu reaction

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Takahashi, H., Shida, T., Hitomi, Y., Iwai, Y., Miyama, N., Nishiyama, K., Sawada, D., & Ikegami, S. (2006). Divergent synthesis of L-sugars and L-iminosugars from D-sugars. Chemistry - A European Journal, 12(22), 5868-5877. https://doi.org/10.1002/chem.200600268