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A scalable approach to obtaining orthogonally protected β-D-idopyranosides
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 4500609
Author(s) Hevey, Rachel; Morland, Alizée; Ling, Chang-Chun
Author(s) at UniBasel Hevey, Rachel
Year 2012
Title A scalable approach to obtaining orthogonally protected β-D-idopyranosides
Journal Journal of Organic Chemistry
Volume 77
Number 16
Pages / Article-Number 6760-6772
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.
Publisher American Chemical Society
ISSN/ISBN 0022-3263 ; 1520-6904
URL https://pubs.acs.org/doi/10.1021/jo300764k
edoc-URL https://edoc.unibas.ch/70096/
Full Text on edoc No
Digital Object Identifier DOI 10.1021/jo300764k
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/22759084
 
   

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