Facile, efficient, and enantiospecific syntheses of 1,1′-N-linked pseudodisaccharides as a new class of glycosidase inhibitors

Tony Kung Ming Shing, Connie S.K. Kwong, Aries W.C. Cheung, Stanton H.L. Kok, Zhifeng Yu, Jianmei Li, Christopher H.K. Cheng

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

This article describes an efficient synthesis of a potent trehalase inhibitor, 1,1′-N-linked pseudodisaccharide 1 (consisting of two valienamines), in 14 steps with an overall yield of 12% and a first synthesis of 2 (consisting of two 2-epi-valienamines) in 15 steps with an overall yield of 24% from (-)-quinic acid. The synthesis involves a stereospecific palladium-catalyzed coupling reaction between an allylic amine and an allylic chloride as the crucial step. The acetonide blocking groups were shown to be the best hydroxyl protecting groups, compatible with the palladium-catalyzed allylic amination reaction that afforded high yields of the 1,1′-N-linked pseudodisaccharides with a minimum amount of an elimination diene side product.

Original languageEnglish
Pages (from-to)15990-15992
Number of pages3
JournalJournal of the American Chemical Society
Volume126
Issue number49
DOIs
Publication statusPublished - 2004 Dec 15
Externally publishedYes

Fingerprint

Glycoside Hydrolases
Palladium
Quinic Acid
Trehalase
Amination
Hydroxyl Radical
Amines
Chlorides
Acids
valienamine

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Shing, T. K. M., Kwong, C. S. K., Cheung, A. W. C., Kok, S. H. L., Yu, Z., Li, J., & Cheng, C. H. K. (2004). Facile, efficient, and enantiospecific syntheses of 1,1′-N-linked pseudodisaccharides as a new class of glycosidase inhibitors. Journal of the American Chemical Society, 126(49), 15990-15992. https://doi.org/10.1021/ja0470158

Facile, efficient, and enantiospecific syntheses of 1,1′-N-linked pseudodisaccharides as a new class of glycosidase inhibitors. / Shing, Tony Kung Ming; Kwong, Connie S.K.; Cheung, Aries W.C.; Kok, Stanton H.L.; Yu, Zhifeng; Li, Jianmei; Cheng, Christopher H.K.

In: Journal of the American Chemical Society, Vol. 126, No. 49, 15.12.2004, p. 15990-15992.

Research output: Contribution to journalArticle

Shing, Tony Kung Ming ; Kwong, Connie S.K. ; Cheung, Aries W.C. ; Kok, Stanton H.L. ; Yu, Zhifeng ; Li, Jianmei ; Cheng, Christopher H.K. / Facile, efficient, and enantiospecific syntheses of 1,1′-N-linked pseudodisaccharides as a new class of glycosidase inhibitors. In: Journal of the American Chemical Society. 2004 ; Vol. 126, No. 49. pp. 15990-15992.
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