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Role of the 4,6-O-acetal in the regio- and stereoselective conversion of 2,3-di-O-sulfonyl-β-D-galactopyranosides to D-idopyranosides

Hevey, Rachel and Chen, Xining and Ling, Chang-Chun. (2013) Role of the 4,6-O-acetal in the regio- and stereoselective conversion of 2,3-di-O-sulfonyl-β-D-galactopyranosides to D-idopyranosides. Carbohydrate Research, 376. pp. 37-48.

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Official URL: https://edoc.unibas.ch/70094/

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Abstract

The recently reported conversion of 2,3-di-O-sulfonyl-D-galactopyranosides to D-idopyranosides has provided an efficient route to obtaining orthogonally-protected idopyranoside building blocks with a β-1,2-cis glycosidic linkage. In an effort to expand the scope of this process and better understand the regio- and stereoselectivity observed in the key di-inversion step of the method, a small library of 4,6-O-acetal protected galactopyranosides has been synthesized and used as substrates in the process, together with a number of substrates that lack the acetal functionality. The results suggest that although the substituent at the acetal center does not contribute to the observed selectivity of the process, the acetal group is indeed required for efficient conversion by reducing the conformational flexibility of the substrate, resulting in enhanced reaction rates at both the O-transsulfonylation and epoxide ring-opening steps.
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:Elsevier
ISSN:0008-6215
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:16 Nov 2020 11:12
Deposited On:16 Nov 2020 11:12

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