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Studies on the 6-homologation of β-D-idopyranosides

Hevey, Rachel and Ling, Chang-Chun. (2017) Studies on the 6-homologation of β-D-idopyranosides. Carbohydrate Research, 445. pp. 65-74.

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Official URL: https://edoc.unibas.ch/70068/

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Abstract

β-D-Idopyranosides are interesting sugars because of their unusual conformational flexibility in the pyranosyl ring, and also their β-1,2-cis-anomeric configuration. Here we report our studies of the regioselective opening of 4,6-O-benzylidene-protected β-D-idopyranosides under reducing conditions, and the subsequent 6-homologation via Swern oxidation and Wittig olefination to afford a 6,7-dideoxy-β-D-ido-hept-6-enopyranoside. This olefination product was found to adopt predominantly; 1; C; 4; conformation in solution by NMR experiments, which places the vinyl group at a more sterically hindered axial position and creates difficulty in subsequent hydroborations.
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:1873-426X
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:09 Apr 2019 15:49
Deposited On:09 Apr 2019 15:49

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