Carbon tetrachloride-free allylic halogenation-mediated glycosylations of allyl glycosides

Das, A and Jayaraman, N (2021) Carbon tetrachloride-free allylic halogenation-mediated glycosylations of allyl glycosides. In: Organic and Biomolecular Chemistry, 19 (42). pp. 9318-9325.

PDF org_blo_che_19_42_9318-9325_2021.pdf - Published Version Restricted to Registered users only Download (826kB) | Request a copy

Abstract

The allylic bromination of allyl glycosides is conducted using NBS/AIBN reagents in (EtO)2CO and PhCF3 solutions, without using CCl4 as a solvent. The activated mixed halo-allyl glycosides led to glycosylations, mediated by a triflate, in a latent-active manner, with the allyl glycosides acting as donors and acceptors. Systematic glycosylation studies are performed with different triflate promoters, non-glycosyl acceptors and various allyl glycosyl donors. One-pot allylic halogenations and subsequent glycosylations are developed in PhCF3 solutions. This newer glycosylation method is utilized to obtain xylo-pyranoside di- and trisaccharides. This journal is © The Royal Society of Chemistry.

Item Type:	Journal Article
Publication:	Organic and Biomolecular Chemistry
Publisher:	Royal Society of Chemistry
Additional Information:	The copyright for this article belongs to Royal Society of Chemistry
Keywords:	Chlorine compounds; Halogenation; Sugars, Allyl glycosides; Allylics; Donor and acceptor; Glycosyl acceptors; Glycosyl donors; Glycosylations; One pot; Pyranosides; Triflates, Glycosylation
Department/Centre:	Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	18 Nov 2021 11:30
Last Modified:	18 Nov 2021 11:30
URI:	http://eprints.iisc.ac.in/id/eprint/70538

Actions (login required)

View Item