A reagent system comprising tetrabutylammonium nitrate-trifluoroacetic anhydride-triethylamine has been developed for the synthesis of 2-nitroglycals from various protected glycals. The base-catalyzed Ferrier rearrangement on tri-O-acetylated 2-nitroglycals has been reported for the first time. Reactivity of these nitroacetates and associated selectivity has been examined, and some of the products have been converted into 2,3-diamino-2,3-dideoxyglycosides and methyl N-acetyl-D-lividosaminide.
Monodispersed CdSe nanoparticles with sufficient luminescence intensity have been prepared by chemical method in the presence of mercaptoacetic acid as a capping agent. Cadmium acetate (Cd(Ac) 2 .2H 2 O) and sodium selenosulfate (Na 2 SeSO 3 ) are used as a cadmium and selenium sources respectively. The resulting nanocrystallites have been characterized by X-Ray Diffraction, UV-Vis absorption spectra and photoluminescence (PL) spectroscopy. The particle size was estimated from broadening of XRD peak using Scherrer's formula and also from effective band gap by absorption peak using effective mass approximation model. The size obtained from XRD and absorption peaks are in agreement with each other. It is observed that the samples consist of separated, well-defined spherical particles and show a small size distribution as well as a characteristic blue shift due to quantum confinement in their optical absorption as well as PL spectra. It is found that the size of CdSe nanoparticles decreases, as the concentration of capping agent is increased. The intensity of PL peak increases and the peak shift towards blue region as the particle size is reduced. The sharp PL spectra also indicate that the nanoparticles are monodispersed.
Azidation of 1,2-anhydro sugars with NaN(3) in CH(3)CN by using a catalytic amount of ceric ammonium nitrate has been accomplished in a regio- and stereoselective manner. Various 1,2-anhydro sugars produced 2-hydroxy-1-azido sugars in good yields which, in turn, were converted to structurally diverse sugar-derived morpholine triazoles and sugar oxazin-2-ones. These sugar derivatives were tested against various commercially available glycosidases, and two of them were found to be active in the micromolar range.
Keywords:Carbohydrates / Iminosugars / Azasugars / Rearrangement / Enzymes / Inhibitors 2-C-Methylene-N-glycosyl amides have been obtained from 2-(hydroxymethyl)glycals through a facile aza-Claisen rearrangement. This rearrangement has also been utilized in the synthesis of L-allo-deoxynojirimycin, a moderate inhibitor of human lysosomal α-mannosidase (IC 50 = 64 µM), and two
A variety of alcohols react with 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabino-hex-1-enopyranose 1 in the presence of a catalytic amount of HClO(4) supported on silica gel to give the corresponding alkyl 3-deoxy-hex-2-enopyranosides 2 in high yield, with short reaction times (10-45 mins) and good alpha-selectivity. Work-up merely involves filtration of the reagent, followed by chromatographic purification of the crude product. This methodology has also been employed in the synthesis of a bicyclic ether, a useful precursor for cyclic polyethers, and a 4-amino-C-glucoside.
Steroids have long played a vital role in organic synthesis because of their unique structural motif and associated biological properties. In recent years, asymmetric synthesis has emerged as a powerful tool for assembling the tetracyclic framework with high levels of molecular diversity. This review summarizes the latest developments in the enantioselective syntheses of both natural and synthetic steroids incorporating the carbocyclic skeleton. The approaches to the synthesis of steroids and related molecules are based primarily on the use of chiral starting materials, the employment of reagent‐controlled asymmetric induction assisted by chiral complexes, chiral Lewis acids or organocatalysts, or the utilisation of chiral auxiliaries.
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