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Issue 14, 2010
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Effective and chemoselective glycosylations using 2,3-unsaturated sugars

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Abstract

Glycosyl donors containing a double bond between C2 and C3 were designed by mimicking the reaction mechanism of lysozyme-initiated hydrolysis of mucopolysaccharides. It was found that, under various glycosylation conditions, the reactivities of 2,3-unsaturated glycosyl acetates were significantly higher, while those of the corresponding 2,3-unsaturated-4-keto glycosyl acetates were much lower than those of the corresponding 2,3-dideoxy (2,3-saturated) glycosyl acetates. Based on these results, chemoselective glycosylations were effectively realized via combinatorial techniques in short-steps using three types of glycosyl donors to construct several types of deoxyoligosaccharides. Furthermore, the highly reactive 2,3-unsaturated glycosyl acetates were found to be useful in the synthesis of the O-glycosides of low reactive tertiary alcohols.

Graphical abstract: Effective and chemoselective glycosylations using 2,3-unsaturated sugars

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Supplementary files

Article information


Submitted
16 Mar 2010
Accepted
12 May 2010
First published
26 May 2010

Org. Biomol. Chem., 2010,8, 3164-3178
Article type
Paper

Effective and chemoselective glycosylations using 2,3-unsaturated sugars

S. Kusumi, K. Sasaki, S. Wang, T. Watanabe, D. Takahashi and K. Toshima, Org. Biomol. Chem., 2010, 8, 3164
DOI: 10.1039/C004204H

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