[reaction: see text] The 2,2,2-trichloroethyl (TCE) group was utilized as the first protecting group for aryl sulfates. Aryl sulfates, protected with the TCE group, were prepared in high yield by reacting phenols with chlorosulfuric acid TCE ester. Deprotection was accomplished using Pd/C-ammonium formate or with Zn-ammonium formate to give aryl sulfate monoesters in high yield. This approach to aryl sulfate synthesis was successfully applied to the construction of estrone sulfate derivatives, which could not be prepared by previous methodologies.
Protection O 0345Synthesis and Protection of Aryl Sulfates Using the 2,2,2-Trichloroethyl Moiety.-The protecting group is introduced for the first time to phenolic hydroxyls. Deprotection according to the methods shown in the scheme allows the preparation of sulfate monoesters.The methology is successfully applied to the construction of estrone sulfate derivatives (X) and (XI), which could not be prepared by previous methodologies. -(LIU, Y.; LIEN, I.--. F.; RUTTGAIZER, S.; DOVE, P.; TAYLOR, S. D.; Org. Lett. 6 (2004) 2, 209-212; Dep. Chem., Univ. Waterloo, Waterloo, Ont. N2L 3G1, Can.; Eng.) -Steudel
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