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Total Synthesis of β-d-ido-Heptopyranosides Related to Capsular Polysaccharides of Campylobacter jejuni HS:4

Zhang, Pengfei and Hevey, Rachel and Ling, Chang-Chun. (2017) Total Synthesis of β-d-ido-Heptopyranosides Related to Capsular Polysaccharides of Campylobacter jejuni HS:4. The Journal of Organic Chemistry, 82 (18). pp. 9662-9674.

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Official URL: https://edoc.unibas.ch/70069/

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Abstract

The 6-deoxy-β-d-ido-heptopyranoside related to the capsular polysaccharides of C. jejuni HS:4 is very remarkable, owing to the unique, multifaceted structural features that have been combined into one molecule, which include (1) the rare ido-configuration, (2) the unusual 7-carbon backbone, and (3) the challenging β-(1→2)-cis-anomeric configuration. Two distinct strategies toward the total synthesis of this interesting target are reported. The first involved establishment of the β-d-idopyranosyl configuration from β-d-galactopyranosides, prior to a C-6-homologation extending the d-hexose to the desired 6-deoxy-d-heptose. However, this approach encountered difficulties due to the significantly reduced reactivity of the 6-position of the β-d-idopyranosides, so instead a second strategy was employed, which involved first carrying out a 6-homologation on the less flexible d-galactopyranose, followed by a very successful conversion to the desired β-d-ido-configuration found in the target heptopyranoside (2). This report is the first successful synthesis of the 6-deoxy-β-d-ido-heptopyranoside, which could possess interesting immunological properties.
Faculties and Departments:05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Pharmazie > Molekulare Pharmazie (Ernst)
05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Pharmazie > Molekulare Pharmazie (Ricklin)
UniBasel Contributors:Hevey, Rachel
Item Type:Article, refereed
Article Subtype:Research Article
ISSN:1520-6904
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:09 Apr 2019 15:57
Deposited On:09 Apr 2019 15:57

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