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Reinvestigation of SnCl catalyzed efficient synthesis of 2,3-unsaturated glycopyranosides.
Carbohydr Res
December 2023
Glycochemistry Laboratory, School of Physical Sciences, Jawaharlal Nehru University, New Delhi, 110067, India; Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, 221005, India. Electronic address:
Article Synopsis
- The Ferrier rearrangement is a highly effective method for synthesizing 2,3-unsaturated glycopyranosides.
- Researchers explored the use of SnCl as a catalyst for direct allylic substitutions on C-3 position of glycals, yielding stereoselective products at low temperatures (0°C).
- A small amount of SnCl was effective in facilitating the reaction with multiple nucleophiles, leading to a range of glycosides with high selectivity and good yields in a shorter time frame.
Structural determination and in vitro tumor cytotoxicity evaluation of five new cycloartane glycosides from Asplenium ruprechtii Sa. Kurata.
Bioorg Chem
September 2020
Shandong Academy of Pharmaceutical Sciences, Jinan 250101, PR China. Electronic address:
Article Synopsis
- - Five new cycloartane glycosides (named aspleniumside A-E) were found in the Asplenium ruprechtii Sa. Kurata plant, traditionally used in folk medicine for treating thromboangitis obliterans in East Asia.
- - The structure and stereo-chemistry of these compounds were examined using advanced NMR techniques, revealing a unique 24R configuration and indicating that the plant's growing environment affects its chemical makeup.
- - The new glycosides were tested for cytotoxicity against cancer cells (HL-60 and HepG2), showing promising results with potential applications in cancer treatment when compared to the standard drug sorafenib.
Reinvestigation of the synthesis of 1-deazauridine.
Nucleosides Nucleotides Nucleic Acids
July 2010
Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan.
A thorough study for the synthesis of 1-deazauridine is described. 3-Bromo-2,6-dimethoxy-5-(beta-D-ribofuranosyl)pyridine, a synthetic precursor for 1-deazauridine, was prepared in seven steps from 2,6-dimethoxypyridine and d-ribose via the ribonolactone approach. Subsequent demethylation was unsuccessful but led to presumable anomerization and isomerization.
View Article and Find Full Text PDFRevision of the O-polysaccharide structure of Yersinia pseudotuberculosis O:1b.
Carbohydr Res
November 2009
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia.
The O-polysaccharide of Yersinia pseudotuberculosis O:1b was reinvestigated using (1)H and (13)C NMR spectroscopy, and the anomeric configuration of the mannose residue at the branching point was revised. The following is the revised structure of the O-polysaccharide: [structure: see the text] where Par stands for 3,6-dideoxy-D-ribo-hexose (paratose). The revised structure of the main chain is shared by the O-polysaccharide of Y.
View Article and Find Full Text PDFReaction pathways of glucose oxidation by ozone under acidic conditions.
Carbohydr Res
July 2009
ICMUB-LIMRES (UMR 5260), Université de Bourgogne, Faculté des Sciences Mirande, F- 21100 Dijon, France.
The ozonation of d-glucose-1-(13)C, 2-(13)C, and 6-(13)C was carried out at pH 2.5 in a semi-batch reactor at room temperature. The products present in the liquid phase were analyzed by GC-MS, HPAEC-PAD, and (13)C NMR spectroscopy.
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