Xu, Chunfa; Loh, Charles C. J. published the artcile< A Multistage Halogen Bond Catalyzed Strain-Release Glycosylation Unravels New Hedgehog Signaling Inhibitors>, Safety of ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-5-yl)methanol, the main research area is glycosylation catalyst glycoside triazole preparation; click alkyne azide triazole cycloaddition catalyst preparation glycoside antitumor.
Halogen bonding (XB) has recently emerged as a promising noncovalent activation mode that can be employed in catalysis. However, methodologies utilizing XB remain rare, and the hydrogen-bonding (HB) catalysis congeners are more widespread in comparison. Herein, we demonstrate a remarkable case whereby employment of XB catalysis in strain-release glycosylation generates O,N-glycosides in excellent anomeric selectivity exceeding HB activation. Deeper investigation unraveled XB catalyst dependencies on multiple stages of the mechanism and a hitherto unknown XB-glycosyl acceptor activation. We present a proof of concept to interrogate sp3-rich glycosidic chem. space for novel biol. activity, by integrating XB-catalyzed construction of a glycosidic compound collection, and evaluating these analogs via cell-based phenotypic screens. We show that XB-catalyzed strain-release glycosylation defines a new class of glycosides that inhibit the hedgehog signaling pathway through a nonsmoothened mode of action, opening new opportunities to combat acquired cancer resistance.
Journal of the American Chemical Society published new progress about 1,3-Dipolar cycloaddition reaction. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Safety of ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-5-yl)methanol.
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