Convenient synthesis of 1,4-thiazane-3-carboxylic acid derivatives.

• 坂井 和夫

• 米田 直人

抄録

A convenient method to synthesize 1, 4-thiazane-3-carboxylic acid derivatives was established. Condensation of L-cysteine methyl ester (2a) with monochloroacetone (3a) followed by reduction with sodium borohydride yielded methyl (3R, 5S)-5-methyl-1, 4-thiazane-3-carboxylate (6a) and its (5R)-methyl isomer (7a) in a ratio of 3.1 : 1. The use of cysteine isopropyl ester (2c) instead of methyl ester (2a) gave the corresponding (5S)-methyl isomer (6e) more stereoselectively. The reaction of chloromethyl ethyl ketone (3b) or α-bromoacetophenone (3c) with 2a gave the corresponding 5-substituted-1, 4-thiazane-3-carboxylates. Hydrolysis and oxidation of 6a yielded cycloalliin (1a).

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 29 (6), 1554-1560, 1981

  公益社団法人 日本薬学会

キーワード

• reduction

詳細情報

• CRID: 1390282679142633472
• NII論文ID: 110003633863
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.29.1554
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/29/6/29_6_1554/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1982193363
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可