We describe the asymmetric synthesis of the 5-amino-5-deoxy-l-fucose (l-fuco-nojirimycin) which appears as a very potent fucosidase inhibitor with a K(i) value of 1 nM.
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http://dx.doi.org/10.1016/j.bmcl.2005.11.100 | DOI Listing |
Org Lett
January 2025
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China.
A series of chiral hybrid diphosphorus ligands incorporating a conformationally flexible tropos diphenylmethane-based phosphoramidite unit have been developed and evaluated in the Rh-catalyzed asymmetric hydrogenation of 2-(1-arylvinyl)anilides and α-enamides, leading to up to >99% yield and 99% enantiomeric excess. Preliminary results from comparative studies showcased the extraordinary catalytic performance of these chiral tropos phosphine-phosphoramidite ligands, with a competency essentially superior to those of well-established ligands with a regular rigid backbone.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Tsinghua University, Chemistry, HeTian Building Dept. of Chemistry, Tsinghua University, Beijing, P. R. China, 100084, Beijing, CHINA.
Expanded heterohelicene composing of alternating linearly and angularly fused multi-resonance (MR) skeleton has garnered wide interest for their promising narrowband emission. Herein, a pair of sym- and asym-expanded heterohelicene isomers are firstly developed by merging boron/oxygen (B/O)-embedded MR triangulene and indolo[3,2,1-jk]carbazole units via one-shot synthesis. Owing to the fully resonating extended helical skeleton, the target heterohelicenes exhibit significantly narrowed spectra bandwidth while emission red-shifting, thus affording deep-blue narrowband emission with peak at around 460 nm, full-width-at-half-maximum (FWHM) of merely 18 nm and near-unity photoluminescence quantum yields.
View Article and Find Full Text PDFNat Commun
January 2025
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Chemical Biology Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing, China.
Helicene-shaped molecules are compelling chemical structures with unique twisted helical chirality and remarkable properties. Although progress occurs in the catalytic asymmetric synthesis of helicene (-like) molecules, the enantioselective synthesis of multiple helicenes, especially four or higher helicity, is still challenging and has yet to be achieved. Herein, we report an organocatalytic [4 + 2] cycloadditions to achieve double S-shaped quadruple helicene-like molecules with high enantioselectivity (up to 96% e.
View Article and Find Full Text PDFActa Crystallogr E Crystallogr Commun
January 2025
Osaka Research Institute of Industrial Science and Technology, 1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan.
The asymmetric unit of the title compound is composed of one host mol-ecule, -4-(1 ,5 -3-aza-1,5(3,9)-dicarbazola-cyclo-octa-phane-3-yl)benzo-nitrile and one di-chloro-methane solvate mol-ecule, CHN·CHCl. The host mol-ecule possesses a planar chirality but crystallizes as a racemate in the space group 2/. It adopts an -configuration, in which two carbazole rings are partially overlapped with a parallel orientation.
View Article and Find Full Text PDFActa Crystallogr E Crystallogr Commun
January 2025
Institut für Anorganische Chemie, Universität Kiel, Max-Eyth.-Str. 2, 24118 Kiel, Germany.
Reaction of Co(NCS) with 4-methyl-pyridine in water leads to the formation of single crystals of the title compound, [Co(NCS)(CHN)] . The asymmetric unit consists of two crystallographically independent thio-cyanate anions and two crystallographically independent 4-methyl-pyridine coligands in general positions, as well as of two different Co cations, of which one is located on a twofold rotational axis, whereas the second occupies a center of inversion. The methyl H atoms in both 4-methyl-pyridine ligands are disordered and were refined using a split model.
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