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Templated Oligosaccharide Synthesis: The Linker Effect on the Stereoselectivity of Glycosylation.

ABSTRACT: A new method for intramolecular oligosaccharide synthesis that is conceptually related to the general molecular clamp approach is introduced. Exceptional ?-selectivity has been achieved in a majority of applications. Unlike other related concepts, this approach is based on the bisphenol A template, which allows one to connect multiple building blocks to perform templated oligosaccharide synthesis with complete stereoselectivity. This principle was demonstrated by the synthesis of an ?,?-linked trisaccharide.

SUBMITTER: Pornsuriyasak P 

PROVIDER: S-EPMC4912053 | biostudies-literature | 2016 May

REPOSITORIES: biostudies-literature

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Templated Oligosaccharide Synthesis: The Linker Effect on the Stereoselectivity of Glycosylation.

Pornsuriyasak Papapida P   Jia Xiao G XG   Kaeothip Sophon S   Demchenko Alexei V AV  

Organic letters 20160426 9

A new method for intramolecular oligosaccharide synthesis that is conceptually related to the general molecular clamp approach is introduced. Exceptional α-selectivity has been achieved in a majority of applications. Unlike other related concepts, this approach is based on the bisphenol A template, which allows one to connect multiple building blocks to perform templated oligosaccharide synthesis with complete stereoselectivity. This principle was demonstrated by the synthesis of an α,α-linked t  ...[more]

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