Topic
Glycal
About: Glycal is a research topic. Over the lifetime, 897 publications have been published within this topic receiving 17422 citations.
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TL;DR: In this paper, a formal electrophilic addition of hypoiodous acid to 3,4,6-tri0-acetyl-o-glucal'3 (1) and 3, 4,di-0,acetyl 6-0-tosyl-D-glocal'4 (2) was described, which can be used for the preparation of Brigl's anhydrides.
16 citations
16 citations
TL;DR: The solid-state structures of C12 bola form isomers adopt shapes very similar to those of bolaforms possessing more extensive hydrogen-bonding networks, indicating that multiple hydrogen bonds in solution are important to formation of stable, discrete nanostructures but that only a few key intermolecular interactions between bolaform headgroups are necessary to determine the structure in the solid state.
Abstract: Glycal-based bolaforms serve as synthetically flexible components of molecular self-assembly. The compounds are prepared in good yield by a Ferrier reaction between triacetylglucal or -galactal or diacetylxylal and a long chain α,ω-diol, followed by deacetylation under Zemplen conditions. The reactions are stereoselective and preferentially afford the α-diastereomer. The bolaforms undergo self-assembly in water or water/dioxane solution to give a variety of nanostructures. In solution, bolaforms with C8 or C10 chains between glucal headgroups form nanoscale vesicles. In contrast, bolaforms with C12 chains exhibit lower solubility and a dynamic self-assembly, forming several different nanoscale structures. However, the solid-state structures of C12 bolaform isomers adopt shapes very similar to those of bolaforms possessing more extensive hydrogen-bonding networks, indicating that multiple hydrogen bonds in solution are important to formation of stable, discrete nanostructures but that only a few key interm...
16 citations
16 citations
TL;DR: Mitsunobu conditions for the efficient synthesis of aryl alpha/beta-sialosides were developed and an oxidative work-up procedure was employed to avoid a cumbersome chromatographic separation from the 2,3-dehydro derivative of sialic acid, which is formed as a side-product.
16 citations