Effective and chemoselective glycosylations using 2,3-unsaturated sugars

Shunichi Kusumi, Kaname Sasaki, Sainan Wang, Tatsuya Watanabe, Daisuke Takahashi, Kazunobu Toshima

研究成果: Article査読

13 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)3164-3178
ページ数15
ジャーナルOrganic and Biomolecular Chemistry
8
14
DOI
出版ステータスPublished - 2010 7月 21

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

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