Document Type

Article

Publication Title

ARKIVOC

Department

Chemistry

ISSN

1551-7012

Volume

2007

Issue

13

DOI

10.3998/ark.5550190.0008.d27

First Page

235

Last Page

251

Publication Date

1-1-2007

Abstract

Three small cluster oligosaccharide mimetics were synthesized, and their CDCl3 solution conformations were determined with NMR experiments. In this paper, we confirmed conformational similarities in rings A and B in all three compounds, and we provide the overall solution geometries. In all cases, an unusual cyclohexane twist-boat conformation with longrange 4 J-(W)-coupling was observed. The origin of the bias towards the twist-boat was attributed primarily to the fused ring system between the cyclohexane ring and the dioxacyclopentane (acetal) including hydrogen bonding. Temperature-annealed molecular dynamics simulations complemented the NMR experiments and supported the overall assignment.

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

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