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ChemInform Abstract: Stereoselective 2-Deoxy-β-O-glycoside Synthesis Based on Remote Activation of Novel Oxathiine Donors.

✍ Scribed by Alessandra Bartolozzi; Giuseppe Capozzi; Stefano Menichetti; Cristina Nativi


Publisher
John Wiley and Sons
Year
2010
Weight
33 KB
Volume
33
Category
Article
ISSN
0931-7597

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Stereoselective 2-Deoxy-β-O-glycoside Sy
✍ Alessandra Bartolozzi; Giuseppe Capozzi; Stefano Menichetti; Cristina Nativi 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 401 KB 👁 1 views

Stable glyco-fused 1,4-oxathiine derivatives, prepared by inverse electron-demand Diels-Alder reactions between suitable 1-glycals and 3-thioxopentane-2,4-dione, have been transformed into unusual glycosyl donors which, after ''remote activation'', react efficiently with glycosyl acceptors to [a] Ce

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Novel Bicyclic Donors for the Synthesis of 2-Deoxy-β-glycosides. -Treatment of the novel heterocyclic donors (V) with a variety of alcohols in the presence of TfOH results in formation of β-glycosides with excellent stereoselectivity. Subsequent desulfurization with Raney-Ni efficiently gives 2-deo