Stereospecific β-l-Rhamnopyranosylation through an SNi-Type Mechanism by Using Organoboron Reagents

Nobuya Nishi, Kazuhiro Sueoka, Kiyoko Iijima, Ryuichi Sawa, Daisuke Takahashi, Kazunobu Toshima

研究成果: Article査読

23 被引用数 (Scopus)

抄録

Stereospecific β-l-rhamnopyranosylations were conducted using a 1,2-anhydro-l-rhamnopyranose donor and mono-ol or diol acceptors in the presence of a glycosyl-acceptor-derived borinic or boronic ester. Reactions proceeded smoothly to provide the corresponding β-l-rhamnopyranosides (β-l-Rhap) with complete stereoselectivity in moderate to high yields without any further additives under mild conditions. Mechanistic studies of the borinic ester mediated glycosylation using 13C kinetic isotope effect (KIE) measurements and DFT calculations were consistent with a concerted SNi mechanism with an exploded transition state. In addition, the present glycosylation method was applied successfully to the synthesis of a trisaccharide, α-l-Rhap-(1,2)-β-l-Rhap-(1,4)-Glcp, derived from Streptococcus pneumoniae serotypes 7B, 7C, and 7D.

本文言語English
ページ(範囲)13858-13862
ページ数5
ジャーナルAngewandte Chemie - International Edition
57
42
DOI
出版ステータスPublished - 2018 10 15

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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