First Total Synthesis of 4-Methylthio-3-butenyl Glucosinolate

• YAMAZOE Sayumi

  Graduate School of Life and Environmental Sciences, University of Tsukuba Institute for Chemical Research and Institute for Integrated Cell-Material Sciences, Kyoto University

• HASEGAWA Koji

  Graduate School of Life and Environmental Sciences, University of Tsukuba

• SHIGEMORI Hideyuki

  Graduate School of Life and Environmental Sciences, University of Tsukuba

抄録

The first total synthesis of 4-methylthio-3-butenyl glucosinolate (MTBG), a natural bioactive compound and a precursor of radish phototropism-regulating substances, was achieved from commercially available 1,4-butanediol. The glucosinolate framework was prepared by coupling of an oximyl chloride derivative and tetraacetyl thioglucose. A methylthio group was introduced to the framework by a Wittig reaction between triphenylphosphonium thiomethylmethylide and an aldehyde intermediate of glucosinolate. The synthetic route should facilitate preparation of various derivatives needed for probe synthesis based on MTBG.

収録刊行物

• Ｂｉｏｓｃｉｅｎｃｅ，　Ｂｉｏｔｅｃｈｎｏｌｏｇｙ，　ａｎｄ　Ｂｉｏｃｈｅｍｉｓｔｒｙ

  Ｂｉｏｓｃｉｅｎｃｅ，　Ｂｉｏｔｅｃｈｎｏｌｏｇｙ，　ａｎｄ　Ｂｉｏｃｈｅｍｉｓｔｒｙ 73 (3), 785-787, 2009

  公益社団法人 日本農芸化学会

キーワード

• 4-methylthio-3-butenyl glucosinolate
• phototropism
• radish
• synthesis
• natural product

詳細情報

• CRID: 1390001206480028160
• NII論文ID: 10027539345
• NII書誌ID: AA10824164
• DOI: 10.1271/bbb.80862
• ISSN: 13476947
• ISSN: 09168451
• NDL書誌ID: 10199529
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I10199529
• Web Site: http://www.tandfonline.com/doi/pdf/10.1271/bbb.80862
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• 抄録ライセンスフラグ: 使用不可