کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5229457 1383663 2008 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Ferric sulfate hydrate-catalyzed O-glycosylation using glycals with or without microwave irradiation
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Ferric sulfate hydrate-catalyzed O-glycosylation using glycals with or without microwave irradiation
چکیده انگلیسی

We have developed a novel glycal-based O-glycosylation reaction, in which the substrates are not only peracetyl glycals but also perbenzyl glucals to afford the corresponding 2,3-unsaturated-O-glycosides via Ferrier rearrangement. The reaction of the perbenzyl glucal with various alcohols catalyzed by ferric sulfate hydrate (Fe2(SO4)3·xH2O) was successfully carried out to give 2,3-unsaturated d-O-glucosides with exclusive α-selectivity and no formation of addition products 2-deoxy hexopyranosides was observed. It is the first report on peralkyl glycal efficiently undergoing Ferrier rearrangement instead of addition of alcohols catalyzed by Lewis acids. Fe2(SO4)3·xH2O is an effective, convenient, and environmentally benign heterogeneous catalyst. It has low catalytic loading and recyclable without significant loss of activity.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 64, Issue 2, 7 January 2008, Pages 339-344
نویسندگان
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