Topic
Glucal
About: Glucal is a research topic. Over the lifetime, 590 publications have been published within this topic receiving 8960 citations. The topic is also known as: D-glucal.
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4 citations
TL;DR: This strategy was successfully extended to the fully O-selective deprotection of acetylated nucleosides where >99% yield was rapidly obtained and no selectivity was observed for the N-deacetylation in amino acids and peptides.
Abstract: A simple, efficient and mild strategy for the complete O-deacetylation of different per-acetylated biomolecules in aqueous media has been described. Different lipases were tested but only the commercial Amano lipase A from Aspergillus niger catalyzed the complete deprotection of peracetylated α-glucose to glucose in excellent yield. The experimental conditions were tested, in particular the pH effect. The reaction was performed at different pHs considering the only enzymatic process was evaluated at pH 5 and the combination of enzymatic and chemical migration process was evaluated at higher pHs. Finally pH 7 and 25 °C were selected as best conditions. Thus this lipase fully hydrolyzed different peracetylated α-glycopyranosides (glucose, mannose, glucal, galactal) with >99% yields, whereas very good deprotecting yields (75–80%) were achieved for different acetylated β-glycopyranosides (galactose, ribofuranose) under these mild conditions. This strategy was successfully extended to the fully O-selective deprotection of acetylated nucleosides where >99% yield was rapidly obtained. No selectivity was observed for the N-deacetylation in amino acids and peptides.
4 citations
TL;DR: In this article, the reaction of ArSCI adducts of exo-glucal with O -and C -nucleophiles leads to a stereoselective preparation of ketopyranoside derivatives and 1, 1- gem -disubstituted C -glucosides, respectively.
4 citations
TL;DR: Enzymatically synthesized D-glucal-6-phosphate inhibits rabbit muscle phosphoglucose isomerase competitively and phosphoglucomutase noncompetitively.
4 citations
TL;DR: In this article, the authors developed simple and efficient protocols for palladium-catalyzed regioselective α-and β-arylations of structurally diverse vinyl ethers.
Abstract: We developed simple and efficient protocols for palladium-catalyzed regioselective α- and β-arylations of structurally diverse vinyl ethers. Both catalytic methods proceed under relatively mild reactions conditions applying to a broad substrate range including more complex compounds providing arylated glucal or isochromene. Lacking the common requirement of a large reagent excess, the transformations are highly economic and limiting the waste production. Results from computational studies (DFT) provided insight into the key factors determining the pronounced regioselectivities of the investigated reactions.
4 citations