Armed-disarmed effect of remote protecting groups on the glycosylation reaction of 2,3-dideoxyglycosyl donors

Satoshi Tomono, Shunichi Kusumi, Daisuke Takahashi, Kazunobu Toshima

研究成果: Article査読

7 被引用数 (Scopus)

抄録

The armed-disarmed effect of remote protecting groups at the C-4 and/or C-6 position(s) on the glycosylation reactions of 2,3-dideoxyglycosyl donors was investigated. It was found that under various glycosylation conditions, 4- or 6-O-Bn 2,3-dideoxyglycosyl donors were much more reactive than the corresponding 4,6-di-O-Bz 2,3-dideoxyglycosyl donors. Based on these results, an effective and chemoselective glycosylation reaction using 4,6-di-O-Bn glycosyl acetate and 4-OH-6-O-Bz glycosyl acetate was realized, producing a 2,3-dideoxydisaccharide in good yield with high α-stereoselectivity.

本文言語English
ページ(範囲)2399-2403
ページ数5
ジャーナルTetrahedron Letters
52
18
DOI
出版ステータスPublished - 2011 5月 4

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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