1,2-trans methyl glycosides can be readily obtained from peracetylated sugars through their initial conversion into glycosyl iodide donors and subsequent exposure of these latter to a slight excess of sodium methoxide in methanol. Under these conditions a varied set of mono- and disaccharide precursors afforded the corresponding 1,2-trans glycosides with concomitant de-O-acetylation in satisfying yields (in the range 59–81%). A similar approach also proved effective when using GlcNAc glycosyl chloride as the donor.
Adaptation of Zemplén's conditions for a simple and highly selective approach to methyl 1,2−trans glycosides / Traboni, Serena; Bedini, Emiliano; Capasso, Domenica; Esposito, Fabiana; Iadonisi, Alfonso. - In: CARBOHYDRATE RESEARCH. - ISSN 0008-6215. - 528:(2023), p. 108824. [10.1016/j.carres.2023.108824]
Adaptation of Zemplén's conditions for a simple and highly selective approach to methyl 1,2−trans glycosides
Traboni, Serena;Bedini, Emiliano;Capasso, Domenica;Esposito, Fabiana;Iadonisi, Alfonso
2023
Abstract
1,2-trans methyl glycosides can be readily obtained from peracetylated sugars through their initial conversion into glycosyl iodide donors and subsequent exposure of these latter to a slight excess of sodium methoxide in methanol. Under these conditions a varied set of mono- and disaccharide precursors afforded the corresponding 1,2-trans glycosides with concomitant de-O-acetylation in satisfying yields (in the range 59–81%). A similar approach also proved effective when using GlcNAc glycosyl chloride as the donor.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.