(3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one | 87641-51-8

• 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-<3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one
• 英文别名: (3S,4R)-3-{(1R)-1-[(tert-Butyldimethylsilyl)oxy]ethyl}-4-[3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl]azetidin-2-one；(4-nitrophenyl)methyl 4-[(2R,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]-3-oxobutanoate
• CAS: 87641-51-8
• 化学式: C₂₂H₃₂N₂O₇Si
• 分子量: 464.591
• InChiKey: CQMSTIDZVBFVOJ-LXGCGDOSSA-N

物化性质

• 沸点：
  583.1±30.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以87%的产率得到(3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)-oxycarbonyl-2-oxopropyl]azetidin-2-one
  参考文献：
  名称：

  .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

  摘要：

  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.

  DOI：

  10.1021/jo00041a032
• 作为产物：
  描述：

  (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<<((4S)-4-ethyl-2-thioxo-1,3-thiazolidin-3-yl)carbonyl>methyl>azetidin-2-one 在 sodium hydroxide 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.17h， 生成 (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one
  参考文献：
  名称：

  .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

  摘要：

  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.

  DOI：

  10.1021/jo00041a032

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.