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: An efficient, enantioselective synthesis of erythro-4-deoxyglycals has been developed using asymmetric aldehyde allylation and tungsten-catalyzed alkynol endo-cycloisomerization as the key steps, which has provided valuable insights into the relationships between glycal structure and reactivity.
Abstract: An efficient, enantioselective synthesis of erythro-4-deoxyglycals has been developed using asymmetric aldehyde allylation and tungsten-catalyzed alkynol endo-cycloisomerization as the key steps. These versatile synthetic scaffolds have been elaborated to a variety of products using stereoselective transformations that are complementary to those available using the corresponding threo glycals. This work has provided valuable insights into the relationships between glycal structure and reactivity. In addition, a new diene-forming side reaction during tungsten-catalyzed alkynol cycloisomerization has been discovered.
34 citations
TL;DR: In this paper, an effective and convenient one-pot procedure, simply involving treatment with boron trifluoride/3-chloroperbenzoic acid (MCPBA), is detailed for the high-yield acquisition of enantiomerically pure dihydropyran-2-ones from mono-and disaccharide-derived glycal and hydroxyglycal esters.
33 citations
TL;DR: A 1-adamantyl thioglycoside derivative of KDN, derived from N-acetylneuraminic acid, carrying a 3,4-O-carbonate protecting group is a highy efficient and α-selective KDN donor on activation with NIS and TfOH in dichloromethane and acetonitrile at −78 °C.
Abstract: A 1-adamantyl thioglycoside derivative of KDN, derived from N-acetylneuraminic acid, carrying a 3,4-O-carbonate protecting group is a highy efficient and α-selective KDN donor on activation with NIS and TfOH in dichloromethane and acetonitrile at −78 °C. Glycosylations conducted with this protecting group do not suffer from competing glycal formation. Seven examples are given, including the use of galactose 3- and 6-hydroxy groups.
33 citations
33 citations
TL;DR: Nucleophilic 1,2-addition of lithiated glycal 9b to functionalized quinone 7 provided, after reductive aromatization, C-arylglycoside 11b, which afforded the tricyclic papulacandin framework.
33 citations