Title

Synthesis and NMR-Characterization of Three Quinamide-Based Disaccharide Mimetics with Unusual Cyclohexane twist-Conformation

Authors

Thuy Trang M. Nguyen, University of the Pacific
Paul H. Gross, University of the PacificFollow
Andreas H. Franz, University of the PacificFollow

Document Type

Article

Publication Title

ARKIVOC

Department

Chemistry

ISSN

1551-7012

Volume

2005

Issue

4

DOI

10.3998/ark.5550190.0006.409

First Page

110

Last Page

128

Publication Date

1-1-2005

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

This work is licensed under a Creative Commons Attribution 4.0 International License.

Recommended Citation

Nguyen, T. T., Gross, P. H., & Franz, A. H. (2005). Synthesis and NMR-Characterization of Three Quinamide-Based Disaccharide Mimetics with Unusual Cyclohexane twist-Conformation. ARKIVOC, 2005(4), 110–128. DOI: 10.3998/ark.5550190.0006.409
https://scholarlycommons.pacific.edu/cop-facarticles/149