A concise, diversity-oriented approach for the synthesis of naturally occurring 3-amino- and 3-nitro-2,3,6-trideoxypyranose derivatives and analogues thereof from simple sugars has been developed. In addition, we investigated the synthesis of various 3-aminoglycosyl donors and their application in glycosylation reactions. These studies led to the successful synthesis of a tetrasaccharide containing four different 3-aminosugar components using ortho-alkynylbenzoate donors.
Challenges for stereoselective
glycosylation of deoxy sugars are
notorious in carbohydrate chemistry. We herein report a novel strategy
for the construction of the less investigated β-glycosidic bonds
of 3,5-trans-3-amino-2,3,6-trideoxy sugars (3,5-trans-3-ADSs), which constitute the core structure of several
biologically important antibiotics. Current protocol leverages a C-3
axial sulfonamide group in 3,5-trans-3-ADSs as a
hydrogen-bond (H-bond) donor and repurposes substoichiometric phosphine
oxide as an exogenous nucleophilic reagent (exNu) to establish an
intramolecular H-bond between the former and the derived α-oxyphosphonium
ion. This pivotal interaction stabilizes the α-face-covered
intermediate to inhibit the formation of the more reactive β-intermediate,
thereby yielding reversed β-selectivity, which is unconventional
for an exNu-mediated glycosylation system. A wide range of substrates
was accommodated, and good to excellent β-selectivities were
ensured by this H-bonding-assisted exNu effect. The robustness of
the current strategy was further attested by the architectural modification
of natural products and drugs containing 3,5-trans-3-ADSs, as well as the synthesis of a trisaccharide unit in avidinorubicin.
The synthesis of Nd-Fe-Co-B by the reduction-diffusion process from neodymium trichloride and its magnetic properties and microstructure have been investigated by x-ray diffraction, scanning electron microscope, and magnetic analysis. According to the thermodynamic data, calcium is capable of reducing neodymium trichloride and then a Nd-Fe-Co-B aHoy is formed by thermal diffusion in the presence of iron, cobalt, and ferro-boron powders at high temperature. The reduction reaction starts at 720 ·C. Thermal diffusion commenced at 800 ·C and forming some Nd 2 Fe ,4 B phase, but the matrix Nd 2 Fe l4 B formed primarily at 860--950 0c.There are three types of phases with different compositions in the sintered Nd-Pe-Co-B RID powders. The oxygen and calcium contents were 0.2 and 0.1 wt. 0/0, respectively. The best yield of Nd-Fe-Co-B powder was up to 98%. The magnetic properties of the sintcred Nd-Fe-Co-B depended on the temperature and time of the reduction-diffusion process. The best magnetic properties obtained were Br = 12.6 kGs, He = 8 kOe, and (BII) m = 36.4 MGOe.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.