Issue 8, 2005
From the journal:

Organic & Biomolecular Chemistry

Glucuronidation of steroidal alcohols using iodosugar and imidate donors

John R. Harding,a   Clare D. King,a   Jennifer A. Perrie,b   Deborah Sinnottb  and  Andrew V. Stachulski*b  

* Corresponding authors

a AstraZeneca UK Ltd., Drug Metabolism and Pharmacokinetics Department, Mereside, Alderley Park, Macclesfield, Cheshire, UK

b The Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, Liverpool, UK
E-mail: stachuls@liv.ac.uk
Fax: 44 (0)151 794 3588
Tel: 44 (0)151 794 3542

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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Article information

DOI
https://doi.org/10.1039/B412217H
Article type
Paper
Submitted
09 Aug 2004
Accepted
23 Feb 2005
First published
15 Mar 2005

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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