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Diastereoselective 1,3-dipolar intramolecular nitrone olefin cycloaddition (INOC) reaction of a sugar-derived allyl alcohol: Synthesis of functionalized aminocyclopentitols.
Carbohydr Res
September 2024
Department of Chemistry, University of Florida, Gainesville, FL, 32611, United States. Electronic address:
The DIBAL-H reduction of the Baylis-Hillman sugar adduct, obtained from 3-O-benzyl-1,2-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose yielded trisubstituted alkenes by eliminating the β-hydroxyl group. Subsequently, the hydrolysis of the isopropylidene acetal to the corresponding hemiacetal was reacted with N-benzyl hydroxylamine hydrochloride to generate the nitrone, which underwent diastereoselective intramolecular 1,3-dipolar nitrone olefin cycloaddition (INOC) to give an isoxazolidine skeleton. The concomitant reductive cleavage of the N-O bond and benzyl group of the fused isoxazolidines afforded new functionalized aminocyclopentitols in good yields.
View Article and Find Full Text PDFFacile Hydrogenative Deprotection of -Benzyl Groups Using a Mixed Catalyst of Palladium and Niobic Acid-on-Carbon.
ACS Omega
February 2020
Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan.
The palladium-on-carbon (Pd/C)-catalyzed hydrogenative deprotection of the -benzyl-protecting group was effectively facilitated by the combined use of niobic acid-on-carbon (NbO/C). NbO/C is an acidic heterogeneous catalyst prepared from NbCl and activated carbon. The catalysts were easily removed from the reaction mixture and reusable.
View Article and Find Full Text PDFOxidative debenzylation of N-benzyl amides and O-benzyl ethers using alkali metal bromide.
Org Lett
July 2014
Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
The oxidative debenzylation of N-benzyl amides and O-benzyl ethers was promoted with high efficiency by a bromo radical formed through the oxidation of bromide from alkali metal bromide under mild conditions. This reaction provided the corresponding amides from N-benzyl amides and carbonyl compounds from O-benzyl ethers in high yields.
View Article and Find Full Text PDFStability of aminooxy glycosides to glycosidase catalysed hydrolysis.
Carbohydr Res
August 2013
School of Pharmacy, University of East Anglia, Norwich Research Park, Norwich, UK.
The stability of the amino(methoxy) beta-glycosidic bond to glycosidase catalysed hydrolysis is reported. Beta-O-benzyl glucose and beta-O-benzyl galactose are substrates hydrolysed by beta-glucosidase and beta-galactosidase from almonds and Escherichia coli, respectively. However their beta-N-benzyl-(O-methoxy)-glucoside and beta-N-benzyl-(O-methoxy)-galactoside derivatives are competitive inhibitors.
View Article and Find Full Text PDFPhosphane-free green protocol for selective nitro reduction with an iron-based catalyst.
Chemistry
May 2011
Natural Plant Products Division, Institute of Himalayan Bioresource Technology (Council of Scientific & Industrial Research), Palampur, Himachal Pradesh, 176 061, India.
Iron phthalocyanine with iron sulfate has been successfully applied for high chemo- and regioselective reduction of aromatic nitro compounds to give the corresponding amines in a green solvent system without using any toxic ligand. The catalytic systems were also compatible with a large range of other reducible functional groups, such as keto, acid, amide, ester, halogen, lactone, nitrile, N-benzyl, O-benzyl, hydroxy, and heterocycles. In the present study, dinitro compounds have been regioselectively reduced to the corresponding amines with high yield.
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