(3R,4R,5R)-3-(1-hydroxyethyl)-4-acetoxy-2-azetidinone

• 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: (3R,4R,5R)-3-(1-hydroxyethyl)-4-acetoxy-2-azetidinone
• 英文别名: 4-acetoxy-3-(1'-hydroxyethyl)azetidine-2-one；4-acetoxy-3-hydroxyethyl-azetidinone；3-(1-Hydroxyethyl)-4-acetoxy-2-azetidinone；[3-(1-hydroxyethyl)-4-oxoazetidin-2-yl] acetate
• 化学式: C₇H₁₁NO₄
• 分子量: 173.169
• InChiKey: RAUONEIRZDXULB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-3-(1-hydroxyethyl)-4-acetoxy-2-azetidinone 、 对氨基苯甲醛 在 diamine functionalized mesoporous silica (AAPTMS(at)MCM-41) 作用下， 以 乙腈 为溶剂， 反应 0.15h， 以95%的产率得到3-(4-aminophenyl)acrylic acid 3-(1-hydroxyethyl)-4-oxoazetidin-2-yl ester
  参考文献：
  名称：

  Novel carbapenem chalcone derivatives: synthesis, cytotoxicity and molecular docking studies

  摘要：

  使用AAPTMS@MCM-41杂化催化剂合成碳青霉烯查尔酮衍生物的高效一锅法合成方案被描述。

  DOI：

  10.1039/c5ob00197h
• 作为产物：
  描述：

  4-acetoxy-3-(1-t-butyl-dimethylsilyloxy)ethyl-2-azetidinone 在 silica gel 作用下， 以 正己烷 为溶剂， 反应 2.0h， 生成 (3R,4R,5R)-3-(1-hydroxyethyl)-4-acetoxy-2-azetidinone
  参考文献：
  名称：

  Novel carbapenem chalcone derivatives: synthesis, cytotoxicity and molecular docking studies

  摘要：

  使用AAPTMS@MCM-41杂化催化剂合成碳青霉烯查尔酮衍生物的高效一锅法合成方案被描述。

  DOI：

  10.1039/c5ob00197h

文献信息

• Antibiotic synthesis
  申请人：Merck & Co., Inc.

  公开号：EP0078026A2

  公开（公告）日：1983-05-04

  A new process involving novel intermediates for the synthesis of antibiotics comprises: 1. acylation of a dianion followed by reduction to introduce an arylhydroxymethyl or alkylhydroxymethyl group; alternatively, alkylation followed by oxidation and reduction to introduce the same group; 2. oxidative decarboxylation to introduce a 4-acetoxy group; 3. silyl enolether chemistry on the acetoxy intermediate using Lewis acids to introduce the side chain, or replacement of the acetoxy group with a triphenylmethylthio group; and 4. ring closures.

  一种涉及新型中间体的抗生素合成新工艺包括 1. 二元离子酰化，然后还原，以引入芳基羟甲基或烷基羟甲基；或者，烷基化，然后氧化和还原，以引入相同的基团； 氧化脱羧，引入 4-乙酰氧基； 3. 使用路易斯酸对乙酰氧基中间体进行硅烯醚化学反应以引入侧链，或用三苯甲硫基取代乙酰氧基；以及 4. 闭环。
• Process for preparing 4-acetoxy-3-hydroxyethylazetizin-2-one derivatives
  申请人：KANEGAFUCHI KAGAKU KOGYO KABUSHIKI KAISHA

  公开号：EP0167154A1

  公开（公告）日：1986-01-08

  A process for preparing 4-acetoxy-3-hydroxyethyl- azetizin-2-one derivative having the general formula (II): wherein R' is a protective group for hydroxy group, which comprises reacting the β-lactam compound having the general formula (I): wherein R' is above, R2, R3 and R4 are a lower alkyl group of C, to C4, phenyl group or aralkyl group and R is a protective group for N, with acetic anhydride in the organic solvent in the presence of base and then removing the protective group for N. 4-Acetoxy-3-hydroxyethylazetizin-2-one derivatives are the useful intermediates for preparing carbapenem β-lactam antibiotics such as thienamycin and penem β-lactam antibiotics.

  一种制备具有通式(II)的 4-乙酰氧基-3-羟乙基氮杂环丁烷-2-酮衍生物的工艺： 其中 R' 为羟基的保护基团，该工艺包括使具有通式（I）的 β-内酰胺化合物反应： 4-乙酰氧基-3-羟乙基氮杂环丁烷-2-酮衍生物是制备碳青霉烯类β-内酰胺抗生素（如噻那霉素和培南β-内酰胺抗生素）的有效中间体。
• beta-Lactam compound and preparing thereof
  申请人：KANEGAFUCHI KAGAKU KOGYO KABUSHIKI KAISHA

  公开号：EP0167155A1

  公开（公告）日：1986-01-08

  The present invention relates to β-lactam compound having the general formula (I): wherein R1 is a protective group for hydroxy group, R2, R3 and R4 are selected from a lower alkyl group of C, to C4, phenyl group and aralkyl group and a process for preparing thereof which comprises reacting enolsilylether having the general forumal (III) wherein R1, R2, R3 and R4 are as above, with chlorosulfonylisocyanate and then reducing the obtained product. β-Lactam compound of the present invention is a useful intermediate for preparing carbapenem β-lactam compound.

  本发明涉及具有通式(I)的β-内酰胺化合物：其中R1是羟基的保护基团，R2、R3和R4选自C,至C4的低级烷基、苯基和芳烷基，以及制备其的工艺，该工艺包括使具有通式(III)的烯醇基醚（其中R1、R2、R3和R4同上）与氯磺酰基异氰酸酯反应，然后还原得到的产物。 本发明的β-内酰胺化合物是制备碳青霉烯类β-内酰胺化合物的有用中间体。
• Beta-lactam compound and process for preparing the same
  申请人：KANEGAFUCHI KAGAKU KOGYO KABUSHIKI KAISHA

  公开号：EP0230248A1

  公开（公告）日：1987-07-29

  A β-lactam compound having the formula (I): wherein R¹, R² and R³ are a member selected from the group consisting of a lower alkyl group having l to 6 carbon atoms, phenyl group and an aralkyl group, a process for preparing the same, which comprises reacting an enolsilylether having the formula (II): wherein R¹, R² and R³ are as defined above, with chlorosulfonylisocyanate and then reducing the obtained product. The β-lactam compound of the present invention is a useful intermediate for preparing carbapenem β-lactam compound.

  一种具有式(I)的β-内酰胺化合物： 其中 R¹、R² 和 R³ 是选自由 l 至 6 个碳原子的低级烷基、苯基和芳烷基组成的组： 其中 R¹、R² 和 R³ 如上定义，与氯磺酰异氰酸酯反应，然后还原得到的产物。本发明的 β-内酰胺化合物是制备碳青霉烯类 β-内酰胺化合物的有用中间体。
• Process for preparing 4-acetoxy-3-hydroxyethylazetidin-2-one derivatives
  申请人：KANEGAFUCHI KAGAKU KOGYO KABUSHIKI KAISHA

  公开号：EP0247378A1

  公开（公告）日：1987-12-02

  A process for preparing a 4-acetoxy-3-­hydroxyethylazetidin-2-one derivative having the formula (II): wherein R¹ is a protective group for the hydroxyl group, which comprises reacting a ß-lactam compound having the formula (I): wherein R¹ is as defined above, and R², R³ and R⁴ are a lower alkyl group having l to 6 carbon atoms, phenyl group or an aralkyl group, with acetic anhydride in an organic solvent in the presence of a low concentration of a substituted pyridine. According to the present invention, there can be obtained 4-acetoxy-3-hydroxy­ethylazetidin-2-one derivatives, which are useful intermediates for preparing carbapenem ß-lactam antibiotics.

  一种制备具有式(II)的 4-乙酰氧基-3-羟乙基氮杂环丁烷-2-酮衍生物的工艺： 其中 R¹ 是羟基的保护基团，该工艺包括使具有式（I）的 ß-内酰胺化合物反应： 其中 R¹ 如上定义，R²、R³ 和 R⁴ 是具有 l-6 个碳原子的低级烷基、苯基或芳烷基。根据本发明，可以得到 4-乙酰氧基-3-羟乙基氮杂环丁烷-2-酮衍生物，它们是制备碳青霉烯ß-内酰胺类抗生素的有用中间体。