Syntheses of small cluster oligosaccharide mimetics

Authors

Andreas H. Franz, University of the PacificFollow
Paul H. Gross, University of the PacificFollow
Vyacheslav V. Samoshin, University of the PacificFollow

Document Type

Article

Publication Title

ARKIVOC

Department

Chemistry

ISSN

1551-7012

Volume

2008

Issue

1

DOI

10.3998/ark.5550190.0009.110

First Page

231

Last Page

308

Publication Date

1-1-2008

Abstract

We designed multiple Small Cluster Oligosaccharide Mimetics (SCOMs) - potential glycosidase inhibitors - to be metabolically stable and small enough to enter cells or bacteria. Therefore, minimal scaffolds (urea, amide, ammonia) or simply non-glycosidic linkages of carbohydrate structures were central to our synthetic strategy, including: (a) coupling of several natural carbohydrate precursors; (b) total syntheses of aminomethyl tetrahydropyrans and their chiral amides with quinic acid; (c) glycopyranosyl cyanide reduction to prepare crowded clusters on a urea scaffold; (d) total syntheses via cycloadditions leading to amide-linked C-glycosides; (e) reduction of nitromethyl C-glycosides; and (f) a synthesis of hydroxylated 1,2- cyclohexanedicarboxylic acids.

Creative Commons License

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

Recommended Citation

Franz, A. H., Gross, P. H., & Samoshin, V. V. (2008). Syntheses of small cluster oligosaccharide mimetics. ARKIVOC, 2008(1), 231–308. DOI: 10.3998/ark.5550190.0009.110
https://scholarlycommons.pacific.edu/cop-facarticles/155