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Article
Synthesis and NMR-Characterization of Three Quinamide-Based Disaccharide Mimetics with Unusual Cyclohexane twist-Conformation
ARKIVOC
  • Thuy Trang M. Nguyen, University of the Pacific
  • Paul H. Gross, University of the Pacific
  • Andreas H. Franz, University of the Pacific
Document Type
Article
Department
Chemistry
DOI
10.3998/ark.5550190.0006.409
Publication Date
1-1-2005
Disciplines
Abstract
The synthesis of amide-linked disaccharide mimetics has been explored starting with carbohydrate-based amines and a protected quinic acid lactone. Benzyl-2-amino-4,6-Obenzylidene-2-deoxy-α/β-D-glucopyranose (12) and D-glucamine (14) were successfully coupled to give the corresponding quinamides (13 and 15), while the quinoylation of Oacetylated L-fucopyranosyl methylamine (7) failed. The latter was prepared from per-O-acetylL-fucopyranose via the improved multigram scale synthesis of the corresponding per-O-acetylL-fucopyranosyl cyanide (3). Compound 3 was subsequently hydrogenated to yield a mixture of compound 7 and the per-O-acetylated bis-(fucopyranosylmethyl) amine (5). The vicinal coupling constants in the NMR spectra of all quinamide products revealed considerable flexibility of the cyclohexane ring in solution and substantial contributions by twist-chair conformations.
Creative Commons License
Creative Commons Attribution 4.0
Citation Information
Thuy Trang M. Nguyen, Paul H. Gross and Andreas H. Franz. "Synthesis and NMR-Characterization of Three Quinamide-Based Disaccharide Mimetics with Unusual Cyclohexane twist-Conformation" ARKIVOC Vol. 2005 Iss. 4 (2005) p. 110 - 128 ISSN: 1551-7012
Available at: http://works.bepress.com/andreas-franz/70/