Pal, Rita and Das, Anupama and Jayaraman, Narayanaswamy (2019) One-pot oligosaccharide synthesis: latent-active method of glycosylations and radical halogenation activation of allyl glycosides. In: PURE AND APPLIED CHEMISTRY, 91 (9). pp. 1451-1470.
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Abstract
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.
| Item Type: | Journal Article |
|---|---|
| Publication: | PURE AND APPLIED CHEMISTRY |
| Publisher: | WALTER DE GRUYTER GMBH |
| Additional Information: | Copyright of this article belongs to WALTER DE GRUYTER GMBH |
| Keywords: | allyl glycosides; carbohydrates; glycosylation; ICS-29; oligosaccharides; oxocarbenium ion; radical halogenation |
| Department/Centre: | Division of Chemical Sciences > Organic Chemistry |
| Date Deposited: | 05 Dec 2019 10:35 |
| Last Modified: | 05 Dec 2019 10:35 |
| URI: | http://eprints.iisc.ac.in/id/eprint/63865 |
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