1-t-Butyldimethylsilyl-4S-carboxymethylazetidin-2-one | 85798-33-0

• 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: 1-t-Butyldimethylsilyl-4S-carboxymethylazetidin-2-one
• 英文别名: 2-[1-[Tert-butyl(dimethyl)silyl]-4-oxoazetidin-2-yl]acetic acid
• CAS: 85798-33-0
• 化学式: C₁₁H₂₁NO₃Si
• 分子量: 243.378
• InChiKey: SJKOWWRLDMKGHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-t-Butyldimethylsilyl-4S-carboxymethylazetidin-2-one 在 4-二甲氨基吡啶 、 氢氟酸 、 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 、 乙腈 为溶剂， 生成 4-<<(Benzyloxy)carbonyl>methyl>-2-azetidinone
  参考文献：
  名称：

  .beta.-Lactams. 1. Highly diastereoselective alkylation of 4-acetoxyazetidin-2-one useful for 1.beta.-methylcarbapenem synthesis

  摘要：

  On the basis of the principle of hard and soft acids and bases, a highly diastereoselective ''asymmetric soft acid-soft base imine alkylation'' was developed. 4-Acetoxyazetidin-2-one (5) was alkylated with the tin(II) enolates of 3-acyl-(4S)-ethyl(and isopropyl)-1,3-thiazolidine-2-thiones 7a,b and 21a,b. The resultant alkylation products (9a,b and 24a,b) could be converted to 17, the key intermediate for the syntheses of both thienamycin (2) and imipenem (3), and to 35, the key intermediate for the synthesis of 1-beta-methylcarbapenem.

  DOI：

  10.1021/jo00041a031
• 作为产物：
  描述：

  1-t-butyldimethylsilyl-4S-benzyloxycarbonylmethylazetidin-2-one 以 甲醇 、 palladium-carbon 为溶剂， 以86.6%的产率得到1-t-Butyldimethylsilyl-4S-carboxymethylazetidin-2-one
  参考文献：
  名称：

  Azetidin-2-one derivatives, and process for production thereof using tin

  摘要：

  公式（I）所代表的一种吲哚啉-2-酮衍生物，其中R.sup.1代表氢原子、较低的烷基基团、芳基、芳基烷基、较低的烷氧基、芳基烷氧基、较低的烷基硫基、芳基烷基硫基或取代氨基团，R.sup.2代表氢原子、较低的烷基基团、芳基或芳基烷基，R.sup.3代表氢原子或具有以下结构的基团：其中R.sup.4代表氢原子或羟基的保护基团；以及其生产方法。

  公开号：

  US04918184A1

文献信息

• The synthesis of 3-(1′-hydroxyethyl)-2-azetidinone-4-yl acetic acid via dianion chemistry - an important intermediate in thienamycin total synthesis
  作者：I Shinkai、T Liu、R.A Reamer、M Sletzinger

  DOI：10.1016/s0040-4039(00)85742-1

  日期：1982.1

  A convenient synthesis of 3-(1′-hydroxyethyl)-2-azetidinone-4-yl acetic acid, one of the key intermediates in the thienamycin total synthesis, based on the chemistry of the dianion derived from readily available 2-azetidinone-4-yl acetic acid is described.

  基于衍生自2-氮杂环丁酮-4的二价阴离子的化学性质，方便合成3-（1'-羟乙基）-2-氮杂环丁酮-4-基乙酸（噻吩霉素全合成的关键中间体之一）描述了乙基乙酸。
• .beta.-Lactams. 1. Highly diastereoselective alkylation of 4-acetoxyazetidin-2-one useful for 1.beta.-methylcarbapenem synthesis
  作者：Yoshimitsu Nagao、Toshio Kumagai、Yunosuke Nagase、Satoshi Tamai、Yoshinori Inoue、Motoo Shiro

  DOI：10.1021/jo00041a031

  日期：1992.7

  On the basis of the principle of hard and soft acids and bases, a highly diastereoselective ''asymmetric soft acid-soft base imine alkylation'' was developed. 4-Acetoxyazetidin-2-one (5) was alkylated with the tin(II) enolates of 3-acyl-(4S)-ethyl(and isopropyl)-1,3-thiazolidine-2-thiones 7a,b and 21a,b. The resultant alkylation products (9a,b and 24a,b) could be converted to 17, the key intermediate for the syntheses of both thienamycin (2) and imipenem (3), and to 35, the key intermediate for the synthesis of 1-beta-methylcarbapenem.
• Azetidin-2-one derivatives, and process for production thereof using tin
  申请人：Lederle (Japan), Ltd.

  公开号：US04918184A1

  公开（公告）日：1990-04-17

  An azetidin-2-one derivative represented by the following formula (I) ##STR1## wherein R.sup.1 represents a hydrogen atom, a lower alkyl group, an aryl group, an aralkyl group, a lower alkoxy group, aralkoxy group, a lower alkylthio group, an aralkylthio group, or a substituted amino group, R.sup.2 represents a hydrogen atom, a lower alkyl group, an aryl group or an aralkyl group, and R.sup.3 represents a hydrogen atom or a group of the formula ##STR2## in which R.sup.4 represents a hydrogen atom or a protective group for the hydroxyl group; and a process for production thereof.

  公式（I）所代表的一种吲哚啉-2-酮衍生物，其中R.sup.1代表氢原子、较低的烷基基团、芳基、芳基烷基、较低的烷氧基、芳基烷氧基、较低的烷基硫基、芳基烷基硫基或取代氨基团，R.sup.2代表氢原子、较低的烷基基团、芳基或芳基烷基，R.sup.3代表氢原子或具有以下结构的基团：其中R.sup.4代表氢原子或羟基的保护基团；以及其生产方法。