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
