(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(N-sulfamoylamino) methylpyrrolidin-3-yl]thio-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carba-2-penem-3-carboxylic acid allyl ester | 148017-61-2

• 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: (1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(N-sulfamoylamino) methylpyrrolidin-3-yl]thio-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carba-2-penem-3-carboxylic acid allyl ester
• 英文别名: prop-2-enyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3S,5S)-1-prop-2-enoxycarbonyl-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 148017-61-2
• 化学式: C₂₂H₃₂N₄O₈S₂
• 分子量: 544.65
• InChiKey: VNNBWRJJCDGJIO-KOWPAETKSA-N

物化性质

• 沸点：
  733.7±70.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  202
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(N-sulfamoylamino) methylpyrrolidin-3-yl]thio-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carba-2-penem-3-carboxylic acid allyl ester 在 四(三苯基膦)钯 N-乙基苯胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以92%的产率得到多尼培南
  参考文献：
  名称：

  EP1852436

  摘要：

  公开号：
• 作为产物：
  描述：

  (2S,4S)-1-allyloxycarbonyl-2-(sulfamoylamino)methyl-4-mercaptopyrrolidine 、 allyl (1R,5R,6S)-2-(diphenoxyphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate 在 N,N-二异丙基乙胺 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 16.0h， 以54%的产率得到(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(N-sulfamoylamino) methylpyrrolidin-3-yl]thio-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carba-2-penem-3-carboxylic acid allyl ester
  参考文献：
  名称：

  EP1595883

  摘要：

  公开号：

文献信息

• A pyrrolidylthiocarbapenem derivative
  申请人：SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD.

  公开号：EP0528678A1

  公开（公告）日：1993-02-24

  A pyrrolidylthiocarbapenem derivative represented by Formula I is provided: wherein R¹ is hydrogen or lower alkyl; R², R³ and R⁴ are hydrogen, lower alkyl which can be substituted or an amino protecting group independently, or R² and R³ together with a nitrogen atom to which R² and R³ are bonded form a saturated or unsaturated cyclic group, or R²and R⁴, or R³ and R⁴ together with two nitrogen atoms and one sulfur atom in the sufamide group form a saturated or unsaturated cyclic group; each cyclic group can further include at least one atom selected from the group consisting of oxygen, sulfur and nitrogen, and each cyclic group can be substituted; X¹ is hydrogen or a hydroxy protecting group; X² is hydrogen, a carboxy protecting group, an ammonio group, an alkali metal or an alkaline-earth metal; and Y² is hydrogen or an amino protecting group.

  提供了一种由式 I 代表的吡咯烷基硫代碳青霉烯类衍生物： 其中 R¹ 为氢或低级烷基；R²、R³ 和 R⁴ 分别为氢、可被取代的低级烷基或氨基保护基团，或 R² 和 R³ 与 R² 和 R³ 键合的一个氮原子一起形成饱和或不饱和环状基团，或 R² 和 R⁴，或 R³ 和 R⁴ 与 sufamide 基团中的两个氮原子和一个硫原子一起形成饱和或不饱和环状基团；每个环状基团可进一步包括至少一个选自氧、硫和氮组成的原子，且每个环状基团可被取代；X¹为氢或羟基保护基团；X²为氢、羧基保护基团、氨基、碱金属或碱土金属；Y²为氢或氨基保护基团。
• A pyrrolidylthiocarbapenem derivative with antibacterial activity
  申请人：SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD.

  公开号：EP0528678B1

  公开（公告）日：2001-05-23
• Process for Producing Carbapenem Derivative and Intermediate Crystal Therefor
  申请人：Uenaka Masaaki

  公开号：US20080171864A1

  公开（公告）日：2008-07-17

  An object of the present invention is to provide a carbapenem synthetic intermediate which is advantageous in an industrial process. There are provided a process for producing Compound (I), or a pharmaceutically acceptable salt, or a solvate, or a crystal thereof, comprising reacting Compound (III) and Compound (IV) in the presence of the secondary amine, and a benzyl alcoholated crystal of Compound (I). There are further provided a method of deprotecting Compound (I) with a Pd catalyst, and a crystal of Compound (IV).
• PROCESS FOR PRODUCING CARBAPENEM DERIVATIVE AND INTERMEDIATE CRYSTAL THEREFOR
  申请人：UENAKA Masaaki

  公开号：US20110224425A1

  公开（公告）日：2011-09-15

  An object of the present invention is to provide a carbapenem synthetic intermediate which is advantageous in an industrial process. There are provided a process for producing Compound (I), or a pharmaceutically acceptable salt, or a solvate, or a crystal thereof, comprising reacting Compound (III) and Compound (IV) in the presence of the secondary amine, and a benzyl alcoholated crystal of Compound (I). There are further provided a method of deprotecting Compound (I) with a Pd catalyst, and a crystal of Compound (IV).
• US5317016A
  申请人：——

  公开号：US5317016A

  公开（公告）日：1994-05-31