(3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[1,1-di(allyloxycarbonyl)ethyl]-2-azetidinone | 150193-38-7

• 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,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[1,1-di(allyloxycarbonyl)ethyl]-2-azetidinone
• 英文别名: bis(prop-2-enyl) 2-[(2S,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]-2-methylpropanedioate
• CAS: 150193-38-7
• 化学式: C₂₁H₃₅NO₆Si
• 分子量: 425.598
• InChiKey: VVNYEYUXBOPUIY-OAGGEKHMSA-N

物化性质

• 沸点：
  493.1±25.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[1,1-di(allyloxycarbonyl)ethyl]-2-azetidinone 生成 (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(RS)-1-(hydroxycarbonyl)ethyl]-2-azetidinone
  参考文献：
  名称：

  Copper-assisted substitution reaction for phenylthio group of a 4-phenylthioazetidinone derivative

  摘要：

  The phenylthio group of 4-phenylthioazetidinone (1) was readily substituted with copper(I) salts of carboxylates, thiocarboxylates, and copper(I) enolates of malonates and beta-ketoesters to give synthetic intermediates (3 and 4) for penem and carbapenem antibiotics.

  DOI：

  10.1016/s0040-4039(00)78210-4
• 作为产物：
  描述：

  4-乙酰氧基氮杂环丁酮 、 diallyl 2-methylmalonate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到(3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[1,1-di(allyloxycarbonyl)ethyl]-2-azetidinone
  参考文献：
  名称：

  使用钯配合物通过脱氧烯丙氧基羰基化简单且高度非对映选择性地合成1β-甲基卡巴培南关键中间体

  摘要：

  通过钯催化的丙二烯丙基丙二酸酯衍生物4a的钯催化的脱烯丙氧羰基化反应，可以轻松地完成关键的1β-甲基卡巴培南中间体1的简单，非对映选择性合成，这很容易从（3S，4R）-4-acetoxy-3-[[R）-1 -（叔丁基二甲基甲硅烷氧基）乙基] -2-氮杂环丁酮2分两个步骤。

  DOI：

  10.1016/0040-4039(94)85196-4

文献信息

• Process for synthesizing 4-substituted azetidinone derivatives
  申请人：Ishiguro Masaji

  公开号：US06867297B1

  公开（公告）日：2005-03-15

  An azetidinone derivative represented by the general formula (1) (wherein OR 1 is a protected hydroxyl group; R 2 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group or a substituted or unsubstituted aromatic group) is reacted with an ester compound represented by the formula (2) (wherein CO 2 R 3 is an esterified carboxyl group; X and Y are the same or different and represent individually a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkenylthio group, a substituted or unsubstituted aralkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkyloxy group, a substituted or unsubstituted alkenyloxy group, a substituted or unsubstituted aralkyloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted silyloxy group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic-thio group, a substituted or unsubstituted heterocyclic-oxy group, a substituted or unsubstituted acyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted thio ester group, a substituted or unsubstituted amide group, a substituted or unsubstituted amino group, a hydrogen atom or halogen atom, or are taken together with each other to form a substituted or unsubstituted cycloalkan-2-on-1-yl group) in the presence of zinc and copper compounds to synthesis a 4-substituted azetidinone derivative represented by the formula (3) (wherein OR 1 , CO 2 R 3 , X and Y are as defined above).

  一种azetidinone衍生物，其通式表示为（1）（其中OR1为受保护的羟基；R2为取代或未取代的烷基、取代或未取代的烯基或取代或未取代的芳香族基），与一个酯化合物反应，该酯化合物的通式表示为（2）（其中CO2R3为酯化的羧基；X和Y分别代表取代或未取代的烷基、取代或未取代的烯基、取代或未取代的芳基烷基、取代或未取代的芳基、取代或未取代的烷硫基、取代或未取代的烯硫基、取代或未取代的芳基硫基、取代或未取代的芳基硫基、取代或未取代的烷氧基、取代或未取代的烯氧基、取代或未取代的芳基氧基、取代或未取代的氧基、取代或未取代的硅氧烷基、取代或未取代的杂环基、取代或未取代的杂环硫基、取代或未取代的杂环氧基、取代或未取代的酰基、取代或未取代的酯基、取代或未取代的硫酯基、取代或未取代的酰胺基、取代或未取代的氨基、氢原子或卤素原子，或彼此相互结合形成取代或未取代的环烷基2-酮1-基），在锌和铜化合物的存在下，合成一种4-取代的azetidinone衍生物，其通式表示为（3）（其中OR1，CO2R3，X和Y如上所定义）。
• PROCESS FOR SYNTHESIZING 4-SUBSTITUTED AZETIDINONE DERIVATIVE
  申请人：Daiichi Suntory Pharma Co., Ltd.

  公开号：EP0638552B1

  公开（公告）日：2003-06-04
• Copper-assisted substitution reaction for phenylthio group of a 4-phenylthioazetidinone derivative
  作者：Tetsuo Shimamoto、Hidekazu Inoue、Takuro Yoshida、Rie Tanaka、Takashi Nakatsuka、Masaji Ishiguro

  DOI：10.1016/s0040-4039(00)78210-4

  日期：1994.8

  The phenylthio group of 4-phenylthioazetidinone (1) was readily substituted with copper(I) salts of carboxylates, thiocarboxylates, and copper(I) enolates of malonates and beta-ketoesters to give synthetic intermediates (3 and 4) for penem and carbapenem antibiotics.
• A simple and highly diastereoselective synthesis of a 1β-methylcarbapenem key intermediate by deallyloxycarbonylation using palladium complexes
  作者：Toshiyuki Murayama、Akifumi Yoshida、Toyohiko Kobayashi、Takashi Miura

  DOI：10.1016/0040-4039(94)85196-4

  日期：1994.4

  A Simple, highly diastereoselective synthesis of the key 1β-methylcarbapenem intermediate 1 has been accomplished via a palladium catalyzed deallyloxycarbonylation of diallyl malonate derivative 4a which was readily prepared from (3S,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone 2 in two steps.

  通过钯催化的丙二烯丙基丙二酸酯衍生物4a的钯催化的脱烯丙氧羰基化反应，可以轻松地完成关键的1β-甲基卡巴培南中间体1的简单，非对映选择性合成，这很容易从（3S，4R）-4-acetoxy-3-[[R）-1 -（叔丁基二甲基甲硅烷氧基）乙基] -2-氮杂环丁酮2分两个步骤。