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o-(p-Methoxyphenylethynyl)phenyl Glycosides: Versatile New Glycosylation Donors for the Highly Efficient Construction of Glycosidic Linkages.
  • Yang Hu, Ke Yu, +5 authors J. Sun
  • Chemistry, Medicine
  • Journal of the American Chemical Society
  • 1 September 2017
A novel alkyne-activation-based glycosylation protocol using o-(p-methoxyphenylethynyl)phenyl (MPEP) glycoside was established and a mechanism for MPEP activation was proposed, supported by systematic mechanistic investigations, including trapping of active intermediates, design of a vital disarmed rhamnosyl donor, and isolation and characterization of the departure species of the leaving group. Expand
Synthetic investigation toward apigenin 5-O-glycoside camellianin B as well as the chemical structure revision.
The first total synthesis of the proposed structure of apigenin-5-O-glycoside camellianin B was achieved, wherein three approaches, one linear and two convergent, were established, through which the synthetic structures were firmly corroborated. Expand
Synthesis of tetrazines from gem-difluoroalkenes under aerobic conditions at room temperature
An efficient and green procedure for the synthesis of tetrazines has been developed based on an old chemistry reported by Carboni in 1958. Both symmetric and asymmetric 3,6-disubstitutedExpand
First Total Synthesis of the Bioactive Arylnaphthyl Lignan 4‐O‐Glycosides Phyllanthusmin D and 4′′‐O‐Acetylmananthoside B
Based on the orchestrated application of PTC and Yu glycosylations, the first total synthesis of arylnaphthalide glycosides, phyllanthusmin D and 4''-O-acetylmananthoside B, which were claimed to beExpand
The 2,2-Dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) Group: A Novel Protecting Group in Carbohydrate Chemistry.
O Orchestrated application of the DMNPA group with other PGs led to the highly efficient synthesis of the glycan of thornasterside A. Expand
Highly efficient synthesis of bioactive oleanane-type saponins.
The synthetic investigation has resulted in the discovery of the effect of branch-sugar incorporation sequence on the overall synthetic efficiency and cytotoxic activity of the obtained triterpenoid saponins, and the preliminary structure-activity relationship was deduced. Expand
Rh-Catalyzed C-H Amidation of 2-Arylbenzo[ d]thiazoles: An Approach to Single Organic Molecule White Light Emitters in the Solid State.
A Rh-catalyzed direct C-H amidation of 2-arylbenzo[ d]thiazoles has been developed. The transformation is characterized by its efficiency, external oxidant-free conditions, and the avoidance of aExpand
Cu-Catalyzed/mediated synthesis of N-fluoroalkylanilines from arylboronic acids: fluorine effect on the reactivity of fluoroalkylamines.
An oxidative coupling reaction of fluoroalkylamines with arylboronic acids has been achieved for the first time. Fluorine has profound influence on the reactivity and fluoroalkylated amines have theExpand
Synthesis of N-Arylsulfonamides by a Copper-Catalyzed Reaction of Chloramine-T and Arylboronic Acids at Room Temperature
A copper-catalyzed Chan–Lam-coupling-like reaction of a (het)arylboronic acid and chloramine-T (or a related compound) has been developed for the synthesis of N -arylsulfonamides at room temperatureExpand