One-pot oligosaccharide synthesis: latent-active method of glycosylations and radical halogenation activation of allyl glycosides
| Autor: | Narayanaswamy Jayaraman, Rita Pal, Anupama Das |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Allylic rearrangement Glycosylation animal structures Stereochemistry General Chemical Engineering organic chemicals Organic Chemistry Oxocarbenium Halogenation Glycosidic bond General Chemistry macromolecular substances carbohydrates (lipids) chemistry.chemical_compound chemistry Moiety Glycosyl lipids (amino acids peptides and proteins) Protecting group |
| Popis: | Chemical glycosylations occupy a central importance to synthesize tailor-made oligo- and polysaccharides of functional importance. Generation of the oxocarbenium ion or the glycosyl cation is the method of choice in order to form the glycosidic bond interconnecting a glycosyl moiety with a glycosyl/aglycosyl moiety. A number of elegant methods have been devised that allow the glycosyl cation formation in a fairly stream-lined manner to a large extent. The latent-active method provides a powerful approach in the protecting group controlled glycosylations. In this context, allyl glycosides have been developed to meet the requirement of latent-active reactivities under appropriate glycosylation conditions. Radical halogenation provides a newer route of activation of allyl glycosides to an activated allylic glycoside. Such an allylic halide activation subjects the glycoside reactive under acid catalysis, leading to the conversion to a glycosyl cation and subsequent glycosylation with a number of acceptors. The complete anomeric selectivity favoring the 1,2-trans-anomeric glycosides points to the possibility of a preferred conformation of the glycosyl cation. This article discusses about advancements in the selectivity of glycosylations, followed by delineating the allylic halogenation of allyl glycoside as a glycosylation method and demonstrates synthesis of a repertoire of di- and trisaccharides, including xylosides, with varied protecting groups. |
| Databáze: | OpenAIRE |
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