Effective and chemoselective glycosylations using 2,3-unsaturated sugars

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

Research output: Contribution to journalArticle

11 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)3164-3178
Number of pages15
JournalOrganic and Biomolecular Chemistry
Volume8
Issue number14
DOIs
Publication statusPublished - 2010 Jul 21

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Glycosylation
sugars
Sugars
acetates
Acetates
glucosides
lysozyme
Muramidase
Glycosides
Glycosaminoglycans
hydrolysis
Hydrolysis
alcohols
reactivity
Alcohols
synthesis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry
  • Medicine(all)

Cite this

Effective and chemoselective glycosylations using 2,3-unsaturated sugars. / Kusumi, Shunichi; Sasaki, Kaname; Wang, Sainan; Watanabe, Tatsuya; Takahashi, Daisuke; Toshima, Kazunobu.

In: Organic and Biomolecular Chemistry, Vol. 8, No. 14, 21.07.2010, p. 3164-3178.

Research output: Contribution to journalArticle

Kusumi, Shunichi ; Sasaki, Kaname ; Wang, Sainan ; Watanabe, Tatsuya ; Takahashi, Daisuke ; Toshima, Kazunobu. / Effective and chemoselective glycosylations using 2,3-unsaturated sugars. In: Organic and Biomolecular Chemistry. 2010 ; Vol. 8, No. 14. pp. 3164-3178.
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