(3R,4R)-4-phenyloxy-3-[(5R)-1'-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

• 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)-4-phenyloxy-3-[(5R)-1'-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one
• 英文别名: (3R,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-phenoxyazetidin-2-one
• 化学式: C₁₇H₂₇NO₃Si
• 分子量: 321.492
• InChiKey: RLPLSESIBBSBRM-IVMMDQJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  sodium phenoxide 、 5-{3-[1-(tert-butyldimethylsilyloxy)ethyl]-4-oxoazetidin-2-yl}-2,2,5-trimethyl-[1,3]dioxane-4,6-dione 以 四氢呋喃 为溶剂， 反应 2.0h， 以96%的产率得到(3R,4R)-4-phenyloxy-3-[(5R)-1'-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one
  参考文献：
  名称：

  1β-Methylcarbapenem intermediates via the thiolysis of a Meldrum's precursor

  摘要：

  5-{3-[1-(tert-Butyidimethylsilyloxy)ethyl]-4-oxo-azetidin-2-yl}-2,2,5-trimethyl-[1,3]dioxane-4,6-dione (3) has been submitted to nucleophilic attack with various nucleophiles. Meldrum's moiety transesterification, C4-substitution, beta -lactam ring opening and Meldrum's moiety decarboxylation were observed. Reaction of 3 with ethanethiol and dimethylaminopyridine in ethanol quantitatively furnished ethyl 2-{3-[1-(tert-butyldimethylsilyloxy)ethyl]-4-oxo-azetidin-2-yl}-thiopropionate as the 1:1 mixture of beta (7a) and alpha (8a) diastereoisomers. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01082-1

文献信息

• 1β-Methylcarbapenem intermediates via the thiolysis of a Meldrum's precursor
  作者：Christophe Jacopin、Mathieu Laurent、Marc Belmans、Luc Kemps、Marcel Cérésiat、Jacqueline Marchand-Brynaert

  DOI：10.1016/s0040-4020(01)01082-1

  日期：2001.12

  5-3-[1-(tert-Butyidimethylsilyloxy)ethyl]-4-oxo-azetidin-2-yl}-2,2,5-trimethyl-[1,3]dioxane-4,6-dione (3) has been submitted to nucleophilic attack with various nucleophiles. Meldrum's moiety transesterification, C4-substitution, beta -lactam ring opening and Meldrum's moiety decarboxylation were observed. Reaction of 3 with ethanethiol and dimethylaminopyridine in ethanol quantitatively furnished ethyl 2-3-[1-(tert-butyldimethylsilyloxy)ethyl]-4-oxo-azetidin-2-yl}-thiopropionate as the 1:1 mixture of beta (7a) and alpha (8a) diastereoisomers. (C) 2001 Elsevier Science Ltd. All rights reserved.