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 article, an iterative and α-selective glycosylation method for 2-deoxyglycosyl and 2,6-dideoxythioglycoside donors based on the DMF modulation concept is described.
31 citations
TL;DR: Synthese du compose du titre a partir de galactal via des intermediaires O-cholestanyl ou O-methyl or O-cresyl-heptopyranosidulose-2onates de methyle qui sont ensuite decarboxyles par le chlorure d'oxathiazolo-1,4,2 [2.3]-pyridinium.
31 citations
TL;DR: In this paper, the tandem Tebbe/Claisen approach to the synthesis of 1-6 linked C-disaccharides was used as a coupling partner for esterification with an allo glycal as substrates.
31 citations
TL;DR: It is established that the configuration at C-5 of the piperidine ring plays a major role in controlling the stereochemical outcome and a short stereocontrolled synthesis of (+)-deoxoprosophylline is achieved using this chemistry.
Abstract: The synthesis of 3,4,6-tri-O-acetyl imino D-glucal 2 from D-glucal is reported. This imino glycal participates in a variety of Lewis acid mediated carbon–carbon bond forming reactions by allylic displacement of the C-3 acetate group by added nucleophiles. Allyl silanes, trimethylsilyl enol ethers, alkenes and dialkyl zinc reagents serve as suitable reaction partners. In all the cases studied, the β-anomer is predominant. Using imino glycal 8, epimeric at C-5, it is established that the configuration at C-5 of the piperidine ring plays a major role in controlling the stereochemical outcome. These results are rationalised by invoking the intermediacy of a conjugated N-acyliminium ion. A short stereocontrolled synthesis of (+)-deoxoprosophylline is achieved using this chemistry. Additionally, imino glucal 2 is transformed into bromo piperidine 16, whose X-ray crystal structure is determined. Bromide 16 participates in palladium catalysed Stille and Suzuki cross-couplings allowing access to C-2 substituted imino sugars 17 and 18. In other studies, imino sugar C-glycosides 21 and 22 are made by combining the Lewis acid mediated carbon–carbon bond forming reactions with stereospecific dihydroxylations.
31 citations
TL;DR: A novel palladium(II)-catalyzed stereoselective synthesis of alpha- and beta-N-glycosyl trichloroacetamides has been developed, which favors the beta-selectivity at the anomeric carbon.
31 citations