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Templated Oligosaccharide Synthesis: Driving Forces and Mechanistic Aspects.

ABSTRACT: We previously communicated that high ?-selectivity that can be achieved in intramolecular glycosylations using a rigid bisphenol A template supplemented with linkers of various lengths. Herein, we present our investigation of the mechanistic aspects of the templated synthesis that helped to design an improved template-linker combination. We demonstrate that bisphenol A as the template in combination with phthaloyl linker allows for superior stereoselectivity and yields in glycosylations. Several mechanistic studies explore origins of the enhanced stereoselectivity and yields achieved using the phthaloyl linker.

SUBMITTER: Jia XG

PROVIDER: S-EPMC5497682 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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Templated Oligosaccharide Synthesis: Driving Forces and Mechanistic Aspects.

Jia Xiao G XG Pornsuriyasak Papapida P Demchenko Alexei V AV

The Journal of organic chemistry 20161207 24

We previously communicated that high α-selectivity that can be achieved in intramolecular glycosylations using a rigid bisphenol A template supplemented with linkers of various lengths. Herein, we present our investigation of the mechanistic aspects of the templated synthesis that helped to design an improved template-linker combination. We demonstrate that bisphenol A as the template in combination with phthaloyl linker allows for superior stereoselectivity and yields in glycosylations. Several ...[more]

PMID: 27978734

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