Glycosidation with a disarmed glycosyl iodide: promotion and scope |
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Authors: | Perrie Jennifer A Harding John R King Clare Sinnott Deborah Stachulski Andrew V |
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Institution: | The Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, Liverpool L 69 7 ZD, UK. |
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Abstract: | reaction: see text] Glucuronyl iodide 1 has been studied in detail as a "disarmed" glycosyl donor. In a model reaction, using N-iodosuccinimide (NIS) as a promoter and 2-phenylethanol as acceptor, best results were obtained using NIS with I(2), followed by trimethylsilyltrifluoromethanesulfonate (TMSOTf). When a series of primary and secondary alcohols was glycosylated using these conditions, yields of 60-83% of beta-glucuronides were obtained. Various "nonheavy" metal salts also effectively catalyzed the model reaction but led to significant amounts of alpha-product with less reactive secondary alcohols. |
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