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Issue 8, 2005
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Glucuronidation of steroidal alcohols using iodosugar and imidate donors

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Abstract

We report a study of the glucuronidation of a number of important steroidal secondary alcohols. The alcohols studied are androsterone 7, epiandrosterone 8, 17-acetoxy-androstane-3α,17β-diol 9, 11α-hydroxyprogesterone 10, and 3-benzoylestradiol 11. These were first glucuronidated using the Schmidt trichloroacetimidate method with variations in acyl substituent (viz. derivatives 2 and 3), Lewis acid catalyst and order of addition. The results are contrasted with those obtained using our recently described glycosyl iodide donor 4, catalysed either by N-iodosuccinimide (NIS) or various metal salts.

Graphical abstract: Glucuronidation of steroidal alcohols using iodosugar and imidate donors

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Publication details

The article was received on 09 Aug 2004, accepted on 23 Feb 2005 and first published on 15 Mar 2005


Article type: Paper
DOI: 10.1039/B412217H
Citation: Org. Biomol. Chem., 2005,3, 1501-1507

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    Glucuronidation of steroidal alcohols using iodosugar and imidate donors

    J. R. Harding, C. D. King, J. A. Perrie, D. Sinnott and A. V. Stachulski, Org. Biomol. Chem., 2005, 3, 1501
    DOI: 10.1039/B412217H

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