(3R,4S)-3-<(1S)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-(carboxymethyl)azetidin-2-one | 102917-34-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R,4S)-3-<(1S)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-(carboxymethyl)azetidin-2-one
• 英文别名: (3R,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-(carboxymethyl)azetidin-2-one；2-[(2S,3R)-3-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]acetic acid
• CAS: 102917-34-0
• 化学式: C₁₃H₂₅NO₄Si
• 分子量: 287.431
• InChiKey: IPVISRLWWJZCAD-QXEWZRGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4S)-3-acetyl-4-ethyl-1,3-thiazolidine-2-thione 生成 (3R,4S)-3-<(1S)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-(carboxymethyl)azetidin-2-one
  参考文献：
  名称：

  NAGAO, JOSIMITSU;KUMAGAYA, TOSIO;KURAMOTO, YASUXIRO

  摘要：

  DOI：

文献信息

• .beta.-Lactams. 2. Diastereoselective alkylative discrimination of racemic 3-substituted 4-acetoxyazetidin-2-ones and its application to the synthesis of a chiral key intermediate for carbapenem syntheses
  作者：Yoshimitsu Nagao、Yunosuke Nagase、Toshio Kumagai、Yasuhiro Kuramoto、Shigeaki Kobayashi、Yoshinori Inoue、Tooru Taga、Hirokazu Ikeda

  DOI：10.1021/jo00041a032

  日期：1992.7

  Alkylation of rac 3-substituted 4-acetoxyazetidin-2-one 4 with chiral tin(II) enolate 8 derived from 3-acetyl-(4S)-ethyl-1,3-thiazolidine-2-thione (ETT) (7) proceeded in a highly diastereoselective manner to give alkylated products 9, 10, and 11 in 42%, 20%, and 9% yields, respectively, after chromatographic purification. Similar alkylation of rac-5 with 8 gave 16, 17, and 18 in 45%, 29%, and 5% yields, respectively. Compound 9 was readily converted to 33, a chiral key intermediate for the synthesis of carbapenems. Analytical separation of rac-4 was effectively done with an HPLC technique employing a chiral column packed with A(S)MBC.
• Highly diastereoselective alkylation onto 4-acetoxy-2-azetidinones employing tin(II) enolates of 3-acyl C-4-chiral 1,3-thiazolidine-2-thiones
  作者：Yoshimitsu. Nagao、Toshio. Kumagai、Satoshi. Tamai、Takao. Abe、Yasuhiro. Kuramoto、Tooru. Taga、Sakae. Aoyagi、Yunosuke. Nagase、Masahito. Ochiai、. et al.

  DOI：10.1021/ja00275a082

  日期：1986.7
• NAGAO, JOSIMITSU;KUMAGAYA, TOSIO;KURAMOTO, YASUXIRO
  作者：NAGAO, JOSIMITSU、KUMAGAYA, TOSIO、KURAMOTO, YASUXIRO

  DOI：——

  日期：——