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A General Approach to O ‐Sulfation by a Sulfur(VI) Fluoride Exchange Reaction
Author(s) -
Liu Chao,
Yang Cangjie,
Hwang Seung,
Ferraro Samantha L.,
Flynn James P.,
Niu Jia
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202007211
Subject(s) - sulfation , chemistry , sulfate , sulfur , monosaccharide , aryl , hydrolysis , molecule , fluoride , hydrogen fluoride , combinatorial chemistry , organic chemistry , inorganic chemistry , biochemistry , alkyl
O‐sulfation is an important chemical code widely existing in bioactive molecules, but the scalable and facile synthesis of complex bioactive molecules carrying O‐sulfates remains challenging. Reported here is a general approach to O‐sulfation by the sulfur(VI) fluoride exchange (SuFEx) reaction between aryl fluorosulfates and silylated hydroxy groups. Efficient sulfate diester formation was achieved through systematic optimization of the electronic properties of aryl fluorosulfates. The versatility of this O‐sulfation strategy was demonstrated in the scalable syntheses of a variety of complex molecules carrying sulfate diesters at various positions, including monosaccharides, disaccharides, an amino acid, and a steroid. Selective hydrolytic and hydrogenolytic removal of the aryl masking groups from sulfate diesters yielded the corresponding O‐sulfate products in excellent yields. This strategy provides a powerful tool for the synthesis of O‐sulfate bioactive compounds.