Efficient synthesis of methyl lycotetraoside, the tetrasaccharide constituent of the tomato defence glycoalkaloid α-tomatine

Jones, Nigel A., Nepogodiev, Sergey A. and Field, Robert A. ORCID: https://orcid.org/0000-0001-8574-0275 (2005) Efficient synthesis of methyl lycotetraoside, the tetrasaccharide constituent of the tomato defence glycoalkaloid α-tomatine. Organic and Biomolecular Chemistry, 3 (17). pp. 3201-3206. ISSN 1477-0520

Full text not available from this repository. (Request a copy)

Abstract

Branched oligosaccharide lycotetraose, β-D-glucopyranosyl-(1→2)- [β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl(1→4) -β-D-galactopyranose, is a key constituent of many steroidal saponins, including glycoalkaloid α-tomatine, which is involved in protection of plants from invading pathogens. A new synthesis of the methyl β-lycotetraoside (2) is described. Key steps of the synthesis include two successive glycosylation reactions of disaccharide acceptor methyl (4,6-O-benzylidene-3-O-p-methoxybenzyl-β-D-glucopyranosyl)-(1→4)-2,3, 6-tri-O-benzyl-β-D-galactopyranoside with readily available benzoylated trichloroacetimidates of α-D-glucopyranose and α,β-D- xylopyranose. This scheme allows sequential glycosylation in one-pot on account of the convenient in situ removal of a p-methoxybenzyl protecting group under the acid conditions of the first glycosylation step. Following deprotection, tetrasaccharide 2 was obtained in 19% yield over eight steps.

Item Type:	Article
Uncontrolled Keywords:	biochemistry,physical and theoretical chemistry,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1300/1303
Faculty \ School:	Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
Related URLs:	http://www.scopus.com/inward/record.url?...
Depositing User:	LivePure Connector
Date Deposited:	10 Sep 2024 12:30
Last Modified:	25 Sep 2024 18:08
URI:	https://ueaeprints.uea.ac.uk/id/eprint/96639
DOI:	10.1039/b508752j

Actions (login required)

View Item