کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1389436 | 982879 | 2009 | 6 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
The role of sugar configuration in the acetolysis of 6-deoxyhexose methyl glycosides
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موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
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چکیده انگلیسی
The acetolysis of several perbenzylated 6-deoxyhexose methyl glycosides under two mild conditions (10 equiv ZnCl2 in 2:1 v/v Ac2O–AcOH at 5 °C; 10:10:1 v/v/v Ac2O–AcOH–TFA at 70 °C) was studied. We focused on the effect of sugar configuration on the competition between mechanisms with activation at exocyclic or endocyclic oxygen site. No effect was detected in acetolysis using the TFA protocol promoting an exo-activation mechanism, which affords 1-O-Ac-pyranosides regardless of sugar configuration. On the contrary, it has a primary role in determining the endo- versus exo-product distribution on ZnCl2-promoted acetolysis.
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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Carbohydrate Research - Volume 344, Issue 17, 23 November 2009, Pages 2406–2411
Journal: Carbohydrate Research - Volume 344, Issue 17, 23 November 2009, Pages 2406–2411
نویسندگان
Luigi Cirillo, Annalida Di Nola, Emiliano Bedini, Michelangelo Parrilli,