論文

2020年7月14日

Indirect synthetic route to α-l-fucosides: Via highly stereoselective construction of α-l-galactosides followed by C6-deoxygenation

Organic and Biomolecular Chemistry
  • Hirotaka Tomida
  • ,
  • Takuya Matsuhashi
  • ,
  • Hide Nori Tanaka
  • ,
  • Naoko Komura
  • ,
  • Hiromune Ando
  • ,
  • Akihiro Imamura
  • ,
  • Hideharu Ishida

18
26
開始ページ
5017
終了ページ
5033
記述言語
掲載種別
研究論文(学術雑誌)
DOI
10.1039/d0ob01128b

We developed an indirect synthetic method for α-l-fucosides. Based on the fact that l-fucose is 6-deoxy-l-galactose, our strategy consists of the stereoselective construction of α-l-galactoside and its conversion to α-l-fucoside via C6-deoxygenation. The formation of α-l-galactoside is strongly directed using 4,6-O-di-tert-butylsilylene(DTBS)-protected l-galactosyl donors. The DTBS-directed α-l-galactosylation showed broad substrate applicability along with excellent coupling yield and α-selectivity. In the C6-deoxygenation of α-l-galactosides, the Barton-McCombie reaction facilitated the conversion to l-fucosides with good yield. To demonstrate the applicability of our method, we synthesized naturally occurring α-l-fucosides. This journal is

リンク情報
DOI
https://doi.org/10.1039/d0ob01128b
PubMed
https://www.ncbi.nlm.nih.gov/pubmed/32573638
Scopus
https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85087741852&origin=inward
Scopus Citedby
https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=85087741852&origin=inward
ID情報
  • DOI : 10.1039/d0ob01128b
  • ISSN : 1477-0520
  • PubMed ID : 32573638
  • SCOPUS ID : 85087741852

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