スギウラ マサハル   Sugiura Masaharu
  杉浦 正晴
   所属   崇城大学  薬学部 薬学科
   崇城大学大学院  薬学研究科 薬学専攻
   職種   教授
言語種別 英語
発行・発表の年月 2002/12
形態種別 原著論文
査読 査読有り
標題 Lewis acid catalyzed ring-opening reactions of sugar-derived semicyclic N,O-acetals
執筆形態 共著
掲載誌名 Helvetica Chimica Acta
掲載区分国外
巻・号・頁 85,pp.3678-3691
著者・共著者 Masaharu Sugiura, Hiroyuki Hagio, Shu Kobayashi
概要 N-(Alkoxycarbonyl)-N-glycosides (polyoxygenated semicyclic N.O-acetals) were efficiently synthesized from regular acetyl or methyl glycosides (glucopyranoside, ribofuranoside, arabinofuranoside, and 2-deoxyribofuranoside) and a carbamate by treatment of trimethylsilyl trifluoromethanesulfonate and 4 Å molecular sieves. It was found that these N-glycosides underwent Lewis acid catalyzed ring-opening reactions with silylated nucleophiles to give ring-opened amino alcohols with good-to-high diastereoselectivity. The reactivity order, 2-deoxyribofuranoside > arabinofuranoside > ribofuranoside > glucopyranoside, was revealed. Ring-opening reductions were also investigated with silanes or diisobutylaluminium hydride. An appropriate reducing agent was found to be dependent on the N-glycosides used. A glycosidase inhibitor, (2S,3R,4R)-2-hydroxymethylpyrrolidine-3,4-diol (7) was synthesized by means of the reactions.
DOI 10.1002/1522-2675(200211)85:11<3678::AID-HLCA3678>3.0.CO;2-0
ISSN 0018019X
PermalinkURL https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=0036943476&origin=inward