Stereoselective synthesis of (+)-5-thiosucrose and (+)-5-thioisosucrose

• Ueda, Atsushi

• Pi, Jinhong

• Makura, Yui

• Tanaka, Masakazu

• Uenishi, Jun'ichi

抄録

+)-5-Thiosucrose 1, a novel isosteric sulfur analog of sucrose, was synthesized stereoselectively for the first time via indirect β-d-fructofuranosidation involving selective β-d-psicofuranosidation, followed by stereo-inversion of the secondary hydroxy group at the C-3 position on the furanose ring. Glycosidation of protected 5-Thio-d-glucose with a d-psicofuranosyl donor provided β-d-psicofuranosyl 5-Thio-α-d-glucopyranoside and that with d-fructofuranosyl donor gave α-d-fructofuranosyl 5-Thio-α-d-glucopyranoside. Two anomeric stereocenters of the glycosyl donor and acceptor were controlled correctly to provide a single disaccharide among four possible anomeric isomers in the glycosylation. Conversion of the resulting disaccharides afforded (+)-5-Thiosucrose 1 and (+)-5-Thioisosucrose 2 in excellent yields, respectively. Inhibitory activities of 1 and 2 against α-glucosidase in vitro were also examined.

RSC Advances, 10(16), pp.9730-9735; 2020

収録刊行物

• RSC Advances

  RSC Advances 10 (16), 9730-9735, 2020-03-06

  Royal Society of Chemistry

詳細情報

• CRID: 1050568772240706048
• NII論文ID: 120006988253
• ISSN: 20462069
• DOI: 10.1039/d0ra01033b
• HANDLE: 10069/39796
• Web Site: https://nagasaki-u.repo.nii.ac.jp/records/626
• Web Site: http://pubs.rsc.org/en/content/articlepdf/2020/RA/D0RA01033B
• 本文言語コード: en
• 資料種別: journal article
• データソース種別:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN