Synthesis of New Chiral Sulfinyldiacetic Acid Derivatives and Attempt at Chemoselective Asymmetric Pummerer Reaction.

• Nagao Yoshimitsu

  Faculty of Pharmaceutical Sciences, The University of Tokushima

• Miyamoto Satoshi

  Faculty of Pharmaceutical Sciences, The University of Tokushima

• Hayashi Kazuhiko

  Faculty of Pharmaceutical Sciences, The University of Tokushima

• Mihira Ado

  Faculty of Pharmaceutical Sciences, The University of Tokushima

• Sano Shigeki

  Faculty of Pharmaceutical Sciences, The University of Tokushima

抄録

(R_S)-1 (85% ee) was prepared by utilizing a porcin pancreatic lipase-promoted hydrolysis of sulfinyldiacetic acid dimethyl ester (8) which was derived from thiodiacetic acid (7). (R_S)-1 (99% ee) and (S_S)-1 (99% ee) were readily obtained by methanolysis of (R_S,S)-12 and (S_S,S)-12 with MeONa in MeOH. (R_S,S)-12 and (S_S,S)-12 were furnished by chromatographic separation of the diastereomeric mixture, obtained by oxidation of thiodiacetic mono-carboxylic acid (11) with 30% H₂O₂ followed by dehydrative condensation of the resultant sulfinyldiacetic mono-carboxylic acid with 4(S)-isopropyl-1,3-thiazolidine-2-thione. (R_S)-1 (99% ee) was successively treated with (TMS)₂NLi, Ac₂O, and TMSOTf to give a major chiral-3 product in 75% ee and in a highly chemoselective manner (chiral-3 : chiral-2=93 : 7).

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 50 (4), 558-562, 2002

  公益社団法人 日本薬学会

キーワード

• chiral sulfoxide
• asymmetric Pummerer reaction
• enzymatic hydrolysis
• optical resolution
• crystallographic structure
• close contact

詳細情報

• CRID: 1390282679140236032
• NII論文ID: 110003616200
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.50.558
• COI: 1:CAS:528:DC%2BD38Xks12ksbk%3D
• ISSN: 13475223
• ISSN: 00092363
• NDL書誌ID: 6120812
• PubMed: 11964012
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I6120812
• Web Site: http://www.jstage.jst.go.jp/article/cpb/50/4/50_4_558/_pdf
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可