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A scalable approach to obtaining orthogonally protected β-D-idopyranosides

Hevey, Rachel and Morland, Alizée and Ling, Chang-Chun. (2012) A scalable approach to obtaining orthogonally protected β-D-idopyranosides. Journal of Organic Chemistry, 77 (16). pp. 6760-6772.

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Official URL: https://edoc.unibas.ch/70096/

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Abstract

A practical method to obtain orthogonally protected D-idopyranose from D-galactose has been developed, which is the first method to enable synthesis of the challenging β-D-idopyranoside linkage. The method relies on a key double inversion at O-2 and O-3 in an easily prepared D-galactose derivative, which proceeds regio- and stereoselectively through a 2,3-anhydrotalopyranoside; reaction using a selection of alkoxides affords exclusively the 3-O-alkylidopyranoside, which can be used to generate an orthogonally protected monosaccharide. The process is scalable and requires minimal purification, so it could be used to produce building blocks to aid in the synthesis of various β-idopyranose-containing oligosaccharide targets to further probe their biological functions.
Faculties and Departments:05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Ehemalige Einheiten 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
Publisher:American Chemical Society
ISSN:0022-3263
e-ISSN:1520-6904
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:16 Nov 2020 11:14
Deposited On:16 Nov 2020 11:14

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