The behaviour of deoxyhexose trihaloacetimidates in selected glycosylations.
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.
Comegna
Daniela
D
Dipartimento di Chimica Organica e Biochimica, Università di Napoli 'Federico II', Complesso Universitario Monte S.Angelo, Via Cintia 4, 80126 Napoli, Italy.
Bedini
Emiliano
E
Di Nola
Annalida
A
Iadonisi
Alfonso
A
Parrilli
Michelangelo
M
D000081:Acetamides; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D003837:Deoxy Sugars / Q000737:chemistry*; D004187:Disaccharides / Q000737:chemistry; D005463:Fluoroacetates; D006031:Glycosylation; D006601:Hexoses / Q000737:chemistry*; D007094:Imides / Q000737:chemistry; D008958:Models, Molecular; D009844:Oligosaccharides / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry
D000081:Acetamides; D003837:Deoxy Sugars; D004187:Disaccharides; D005463:Fluoroacetates; D006601:Hexoses; D007094:Imides; D009844:Oligosaccharides; C030688:trifluoroacetamide; D014269:Trifluoroacetic Acid