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Regio- and Stereoselective Synthesis of 1-/3-Sulfone Sugars Controlled by the Amount of SnCl4
Yimin Xiang1, Jing Xu1, Tao Xiong1
1Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, China.
Abstract:
A SnCl4-mediated regioselective sulfonylation of glycal donors with sulfinic acids enables stereodivergent synthesis of 1-sulfone sugars (0-10 mol % SnCl4) or 3-sulfone sugars (1 equiv of SnCl4), respectively. Mechanistic studies reveal that sulfinic acid can activate the C3 leaving group alone to form sulfone glycosides, while excess SnCl4 promotes the 1,3-shift to afford 3-sulfone sugars. The protocol exhibits broad substrate scope, including late-stage modification of natural products, with excellent regio-/stereoselectivity.
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