Silyl-assisted 1,2-cis-α-glucosylation for the synthesis of a triglucoside moiety in high-mannose-type oligosaccharidesElectronic supplementary information (ESI) available: Experimental details and characterization data for new compounds. See DOI: 10.1039/c5ra16659d

A highly stereoselective 1,2- cis -α-glucosylation reaction was developed, in which the use of a strongly electron-donating tert -butyldimethylsilyl protecting group on the C-2 hydroxy group of a glycosyl donor enhanced the α -favoured transition state, and thus resulted in high yield and α -selecti...

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Main Authors: Totani, Kiichiro, Shinoda, Yuki, Shiba, Masaaki, Iwamoto, Shogo, Koizumi, Akira, Matsuzaki, Yuji, Hirano, Makoto
Format: Article
Language:English
Online Access:Get full text
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Summary:A highly stereoselective 1,2- cis -α-glucosylation reaction was developed, in which the use of a strongly electron-donating tert -butyldimethylsilyl protecting group on the C-2 hydroxy group of a glycosyl donor enhanced the α -favoured transition state, and thus resulted in high yield and α -selectivity. Synthetic utility of this α -glucosylation was demonstrated by the generation of a triglucoside moiety in high-mannose-type oligosaccharides. We developed a new 1,2- cis -α-glucosylation reaction, mediated by enhancing the α-favoured transition state via an electron-donating form the TBS group.
ISSN:2046-2069
DOI:10.1039/c5ra16659d