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.
Papers published on a yearly basis
Papers
More filters
TL;DR: In this article, a thermophilic and thermostable β-glycosyl hydrolase from the archeon Sulfolobus solfataricus and glucal or galactal as donors was used for the synthesis of 2-deoxy glycosides and, for the first time, of 2deoxygalactosides.
Abstract: The synthesis of 2-deoxyglycosides and, for the first time, of 2-deoxygalactosides is reported using a thermophilic and thermostable β-glycosyl hydrolase from the archeon Sulfolobus solfataricus and glucal or galactal as donors. The yields observed with alkyl acceptors confirmed that the robustness of the biocatalyst is of great help in designing practical syntheses of pure β-anomers of 2-deoxy derivatives of 4-penten-1-ol (obtained in 80% yield at 20 fold molar excess) and 3,4-dimethoxybenzyl alcohol (obtained in 19% yield at 3.3 fold molar excess). The attachment of 2-deoxyglyco units was performed on various pyranosidic acceptors (p-nitrophenyl α-d-glucopyranoside, o-nitrophenyl 2-deoxy-N-acetyl-α-d-glucosamine and p-nitrophenyl 2-deoxy-N-acetyl-β-d-glucosamine). At low molecular excesses of the acceptors, satisfactory yields (20-40%) of chromophoric 2-deoxy di- and trisaccharides were obtained. The different regioselectivity of our enzyme with respect to mesophilic counterparts reflects the importance...
6 citations
TL;DR: In this paper, a method for C-glycosidation with various silylacetylenes to d -glucal by iodine molecule via iodo-oxonium intermediates provided exclusively the α-acetylene glycoside products.
Abstract: A convenient method for C-glycosidation (alkynylation) with various silylacetylenes to d -glucal by iodine molecule via iodo–oxonium intermediates provided exclusively the α-acetylene glycoside products. Eleven successful examples are shown under this condition.
6 citations
TL;DR: Ferrier's carbocyclization of 4-O-acetyl-3-azido gave (2S,3R,5R)−2-acetoxy−3]-azido−5-hydroxycyclohexanone which was converted into oxime.
6 citations
6 citations
TL;DR: In this paper, the corresponding oxadiene, prepared from the starting perbenzylated α-d -mannopyranosylethanal was subjected to stereoselective cycloaddition reactions with R and S methyl (ethenyloxy)(phenyl)acetates.
6 citations