(4S)-Ethyl-1,3-thiazolidine-2-thione | 42163-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-Ethyl-1,3-thiazolidine-2-thione
• 英文别名: (4S)-4-Ethyl-1,3-thiazolidine-2-thione
• CAS: 42163-68-8
• 化学式: C₅H₉NS₂
• 分子量: 147.265
• InChiKey: UBKTWHKJHPIXFH-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one 、 (4S)-Ethyl-1,3-thiazolidine-2-thione 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以75%的产率得到(3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-<((4S)-4-ethyl-2-thoxo-1,3-thiazolidin-3-yl)carbonyl>ethyl>azetidin-2-one
  参考文献：
  名称：

  .beta.-Lactams. 3. Asymmetric total synthesis of new non-natural 1.beta.-methylcarbapenems exhibiting strong antimicrobial activities and stability against human renal dehydropeptidase-I

  摘要：

  Asymmetric synthesis of 11, the precursor to chiral (3R,4R)-3-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-4-acetoxyazetidin-2-one (3) was achieved by utilizing a highly diastereoselective aldol-type reaction of acetaldehyde and the chiral tin(II) enolate of 5. Similar diastereoselective alkylations of chiral and achiral tin(II) enolates 13a-d with chiral 3 were also performed to obtain the desired alkylated azetidin-2-ones (17a-d). Compounds 17a,b were successfully converted to new, non-natural 1-beta-methylcarbapenems 1a and 1b, which exhibited strong and wide-ranging antimicrobial activities and excellent stability against human renal dehydropeptidase-I.

  DOI：

  10.1021/jo00041a033
• 作为产物：
  描述：

  二硫化碳 、 (S)-(+)-2-氨基-1-丁醇 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以82.5%的产率得到(4S)-Ethyl-1,3-thiazolidine-2-thione
  参考文献：
  名称：

  New C-4-chiral 1,3-thiazolidine-2-thiones: excellent chiral auxiliaries for highly diastereo-controlled aldol-type reactions of acetic acid and .alpha.,.beta.-unsaturated aldehydes

  摘要：

  DOI：

  10.1021/jo00362a047

文献信息

• NAGAO, JOSIMITSU;FUDZITA, EHJITI;XAGIVARA, YUITI;KUMAGAYA, TOSIO
  作者：NAGAO, JOSIMITSU、FUDZITA, EHJITI、XAGIVARA, YUITI、KUMAGAYA, TOSIO

  DOI：——

  日期：——
• New C-4-chiral 1,3-thiazolidine-2-thiones: excellent chiral auxiliaries for highly diastereo-controlled aldol-type reactions of acetic acid and .alpha.,.beta.-unsaturated aldehydes
  作者：Yoshimitsu Nagao、Yuichi Hagiwara、Toshio Kumagai、Masahito Ochiai、Takehisa Inoue、Keiji Hashimoto、Eiichi Fujita

  DOI：10.1021/jo00362a047

  日期：1986.6
• .beta.-Lactams. 3. Asymmetric total synthesis of new non-natural 1.beta.-methylcarbapenems exhibiting strong antimicrobial activities and stability against human renal dehydropeptidase-I
  作者：Yoshimitsu Nagao、Yunosuke Nagase、Toshio Kumagai、Hiroshi Matsunaga、Takao Abe、Osamu Shimada、Takaaki Hayashi、Yoshinori Inoue

  DOI：10.1021/jo00041a033

  日期：1992.7

  Asymmetric synthesis of 11, the precursor to chiral (3R,4R)-3-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-4-acetoxyazetidin-2-one (3) was achieved by utilizing a highly diastereoselective aldol-type reaction of acetaldehyde and the chiral tin(II) enolate of 5. Similar diastereoselective alkylations of chiral and achiral tin(II) enolates 13a-d with chiral 3 were also performed to obtain the desired alkylated azetidin-2-ones (17a-d). Compounds 17a,b were successfully converted to new, non-natural 1-beta-methylcarbapenems 1a and 1b, which exhibited strong and wide-ranging antimicrobial activities and excellent stability against human renal dehydropeptidase-I.