5-(tert-butyldimethylsilyloxy)-4-carbamoyl-2-methylhex-2-enethioic acid ethyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-(tert-butyldimethylsilyloxy)-4-carbamoyl-2-methylhex-2-enethioic acid ethyl ester
• 英文别名: S-ethyl (E,4S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-4-carbamoyl-2-methylhex-2-enethioate
• 化学式: C₁₆H₃₁NO₃SSi
• 分子量: 345.579
• InChiKey: VKTGHYSLUNBGCB-NQYVGZPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  94.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-{3-[1-(tert-butyldimethylsilyloxy)ethyl]-4-oxoazetidin-2-yl}-2,2,5-trimethyl-[1,3]dioxane-4,6-dione 、 乙硫醇钠 在 18-冠醚-6 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以95%的产率得到5-(tert-butyldimethylsilyloxy)-4-carbamoyl-2-methylhex-2-enethioic acid ethyl ester
  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.