The behaviour of deoxyhexose trihaloacetimidates in selected glycosylations |
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Authors: | Comegna Daniela Bedini Emiliano Di Nola Annalida Iadonisi Alfonso Parrilli Michelangelo |
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Institution: | Dipartimento di Chimica Organica e Biochimica, Università di Napoli 'Federico II', Complesso Universitario Monte S.Angelo, Via Cintia 4, 80126 Napoli, Italy. |
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Abstract: | Armed deoxyhexose glycosyl donors are very reactive and sometimes too uncontrollably activated in glycosylation reactions; yields can be thereby reduced, especially when unreactive glycosyl acceptors are involved. In this paper, the behaviour of a range of deoxyhexose trihaloacetimidate (trichloro- and N-phenyl trifluoro-) donors is compared in some selected glycosylations towards biologically relevant targets. The selected N-phenyl trifluoroacetimidates often afforded best results in terms of both donor synthesis and glycosylation yield. |
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Keywords: | Glycosylations Deoxysugars Glycosyl N-phenyl trifluoroacetimidates Glycosyl trichloroacetimidates |
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