Adaptation of Zemplén's conditions for a simple and highly selective approach to methyl 1,2-trans glycosides.
- Resource Type
- Academic Journal
- Authors
- Traboni S; Department of Chemical Sciences, University of Naples Federico II, Via Cinthia 4, 80126, Naples, Italy.; Bedini E; Department of Chemical Sciences, University of Naples Federico II, Via Cinthia 4, 80126, Naples, Italy.; Capasso D; Center for Life Sciences and Technologies (CESTEV), University of Naples Federico II, 80145, Naples, Italy.; Esposito F; Department of Chemical Sciences, University of Naples Federico II, Via Cinthia 4, 80126, Naples, Italy.; Iadonisi A; Department of Chemical Sciences, University of Naples Federico II, Via Cinthia 4, 80126, Naples, Italy. Electronic address: iadonisi@unina.it.
- Source
- Publisher: Elsevier Country of Publication: Netherlands NLM ID: 0043535 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1873-426X (Electronic) Linking ISSN: 00086215 NLM ISO Abbreviation: Carbohydr Res Subsets: MEDLINE
- Subject
- Language
- English
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.
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
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