Journal ArticleDOI
Microwave assisted stereospecific synthesis of d-erythro-l-gluco-nonulose
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TLDR
In this article, a branched sugar bearing a CH2OH group at C-2 provides access to a nine-carbon sugar in a single step through a stereospecific isomerization.Abstract:
A convenient, highly efficient synthesis of d -erythro- l -gluco-nonulose from a new 2-C-(hydroxymethyl) branched-chain aldose is presented. The nucleophilic addition of the appropriately protected aldose to formaldehyde afforded 2-C-(hydroxymethyl)- d -erythro- l -manno-octose. The branched sugar bearing a CH2OH group at C-2 provides access to a nine-carbon sugar in a single step through a stereospecific isomerization. The isomerization exploited the catalytic effect of molybdate ions and microwave irradiation. The structure of the product was analyzed by NMR spectra and quantum-chemical DFT calculations. DFT-computed proton–proton coupling constants were found to be comparable with the experimentally obtained coupling constants and agreed with the pyranose form of this branched-chain aldose.read more
Citations
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Journal ArticleDOI
Isomerization as a route to rare ketoses: the beneficial effect of microwave irradiation on Mo(VI)-catalyzed stereospecific rearrangement
TL;DR: In this paper, a Mo(VI)-catalyzed isomerization of easily accessible 2-C-(hydroxymethyl)-branched aldoses to rare ketoses was achieved in 3min using microwave flash heating.
Journal ArticleDOI
Microwave-assisted stereospecific intramolecular rearrangement of (1→6)-linked disaccharides catalyzed by Mo(VI)
TL;DR: In this article, three (1→6)-linked disaccharides, melibiose, isomaltose and palatinose, were converted into their isomers via intramolecular rearrangement catalyzed by Mo(VI).
Journal ArticleDOI
A new approach to Amadori ketoses via MoVI-catalyzed stereospecific isomerization of 2-C-branched sugars bearing azido function in a microwave field
TL;DR: In this paper, a branched-chain aldose bearing an azido group at the C-2 position provides access to the corresponding 1-deoxy-1-azido- and 1 -deoxy -1-amino ketoses in a single step via stereospecific isomerization.
Journal ArticleDOI
Water promoted, microwave-assisted oxidative novel deamination of N-aminoquinazolinones
TL;DR: In this paper, a novel deamination of 2-alkyl/aryl 3-amino-4(3 H )-quinazolinones series using aqueous KMnO 4 under thermal condition and microwave irradiation is described.
Book ChapterDOI
Transition-Metal-Catalyzed Transformation of Monosaccharides and Polysaccharides
TL;DR: In this paper, the authors give an overview of transition-metal-catalyzed transformations of various mono- and polysaccharides into enantiopure compounds, fine chemicals, and building blocks suitable for industrial application.
References
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Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis
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Density-functional theory of atoms and molecules
TL;DR: In this paper, a review of current studies in density functional theory and density matrix functional theory is presented, with special attention to the possible applications within chemistry, including the concept of an atom in a molecule, calculation of electronegativities from the Xα method, pressure, Gibbs-Duhem equation, Maxwell relations and stability conditions.