Concise synthesis of 1,3-di-O-substituted tetrahydropyran derivatives as conformationally stable pyranose mimetics

Authors

Laurel K. Mydock, Department of Chemistry and Biochemistry
Christopher D. Spilling, Department of Chemistry and Biochemistry
Alexei V. Demchenko, Department of Chemistry and BiochemistryFollow

Document Type

Article

Keywords

Carbohydrates, Conformation, Total synthesis

Abstract

A practical synthetic route to 1,3-di-O-substituted tetrahydropyrans has been developed. An important feature of these obtained glycomimetics is the bulky t-butyl functionality at the C-4 position, which imposes a chair conformation as the lowest energy conformer, making these compounds ideal pyranose mimetics. © 2010 Académie des sciences.

Publication Date

2-1-2011

Publication Title

Comptes Rendus Chimie

ISSN

16310748

Volume

14

Issue

2-3

First Page

301

Last Page

306

Rights

CC BY

DOI

10.1016/j.crci.2010.05.016

Funding Number

CHE-0547566

Funding Sponsor

National Science Foundation

Recommended Citation

Mydock, Laurel K.; Spilling, Christopher D.; and Demchenko, Alexei V., "Concise synthesis of 1,3-di-O-substituted tetrahydropyran derivatives as conformationally stable pyranose mimetics" (2011). Chemistry & Biochemistry Faculty Works. 113.
DOI: https://doi.org/10.1016/j.crci.2010.05.016
Available at: https://irl.umsl.edu/chemistry-faculty/113