(3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<(2-thioxo-4,4-dimethyl-1,3-thiazolidin-3-yl)carbonyl>ethyl>azetidin-2-one | 115026-49-8

• 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: (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<(2-thioxo-4,4-dimethyl-1,3-thiazolidin-3-yl)carbonyl>ethyl>azetidin-2-one
• 英文别名: (3S,4R)-3-{(1R)-1-[(tert-Butyldimethylsilyl)oxy]ethyl}-4-{(1R)-1-[(2-thioxo-4,4-dimethyl-1,3-thiazolidin-3-yl)carbonyl]ethyl}azetidin-2-one；(3S,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(2R)-1-(4,4-dimethyl-2-sulfanylidene-1,3-thiazolidin-3-yl)-1-oxopropan-2-yl]azetidin-2-one
• CAS: 115026-49-8
• 化学式: C₁₉H₃₄N₂O₃S₂Si
• 分子量: 430.708
• InChiKey: WXQODQBBCJKWTA-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-乙酰氧基氮杂环丁酮 、 3-Propionyl-4,4-dimethyl-1,3-thiazolidine-2-thione 在 N-乙基哌啶 、 tin(II) trifluoromethanesulfonate 作用下， 以80%的产率得到(3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<(2-thioxo-4,4-dimethyl-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

文献信息

• .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.