2-{3-[1-(tert-butyldimethylsilyloxy)ethyl]-4-oxoazetidin-2-yl}thiopropionic acid ethyl ester | 155933-04-3

• 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: 2-{3-[1-(tert-butyldimethylsilyloxy)ethyl]-4-oxoazetidin-2-yl}thiopropionic acid ethyl ester
• 英文别名: S-ethyl (2R)-2-[(2S,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]propanethioate
• CAS: 155933-04-3
• 化学式: C₁₆H₃₁NO₃SSi
• 分子量: 345.579
• InChiKey: ZPNRBIFZDRTIDT-FDYHWXHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-{3-[1-(tert-butyldimethylsilyloxy)ethyl]-4-oxoazetidin-2-yl}thiopropionic acid ethyl ester 在 三乙基硅烷 、 sodium hydroxide 、 palladium on activated charcoal 作用下， 以 甲苯 为溶剂， 生成 [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((S)-2-[1,3]dithian-2-ylidene-1-methyl-ethyl)-4-oxo-azetidin-1-yl]-hydroxy-acetic acid benzhydryl ester
  参考文献：
  名称：

  乙烯酮二硫缩醛封端的环化反应合成1β-甲基卡巴姆的新方法

  摘要：

  用烯酮二硫缩醛终止剂将醇5环化成碳青霉烯6是通过由相应的甲磺酸酯生成的酰基酰亚胺离子实现的。Carbapenams 6转化到碳青霉烯7通过1个Ò 2烯酮二硫缩醛部分，enolphosphorylation，和加成-消除过程的介导的裂解。

  DOI：

  10.1016/0040-4039(96)01785-6
• 作为产物：
  描述：

  4-乙酰氧基氮杂环丁酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 10.0h， 生成 2-{3-[1-(tert-butyldimethylsilyloxy)ethyl]-4-oxoazetidin-2-yl}thiopropionic 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

• Seki, Masahiko; Kondo, Kazuhiko; Iwasaki Tameo, Journal of the Chemical Society. Perkin transactions I, 1996, # 1, p. 3 - 6
  作者：Seki, Masahiko、Kondo, Kazuhiko、Iwasaki Tameo

  DOI：——

  日期：——
• A new synthesis of 1β-methylcarbapenems using NBS-promoted cyclization as a key step
  作者：Osamu Sakurai、Masami Takahashi、Tsuyoshi Ogiku、Masahito Hayashi、Hiroshi Horikawa、Tameo Iwasaki

  DOI：10.1016/s0040-4039(00)73421-6

  日期：1994.8

  A novel construction of 1 beta-methylcarbapenem skeleton has been achieved by use of N-bromosuccinimide(NBS)-promoted cyclization as a key step. The mechanism of the stereospecific cyclization leading to 1 beta-methylcarbapenam is also discussed.
• 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.
• A new synthetic method of 1β-methylcarbapenems utilizing the ketene dithioacetal-terminated cyclization
  作者：Osamu Sakurai、Hiroshi Horikawa

  DOI：10.1016/0040-4039(96)01785-6

  日期：1996.10

  Cyclization of alcohols 5 with the ketene dithioacetal terminator into carbapenams 6 was accomplished via the acyliminium ion generated from the corresponding mesylates. Carbapenams 6 were transformed into carbapenem 7 through 1O2-mediated cleavage of the ketene dithioacetal portion, enolphosphorylation, and addition-elimination processes.

  用烯酮二硫缩醛终止剂将醇5环化成碳青霉烯6是通过由相应的甲磺酸酯生成的酰基酰亚胺离子实现的。Carbapenams 6转化到碳青霉烯7通过1个Ò 2烯酮二硫缩醛部分，enolphosphorylation，和加成-消除过程的介导的裂解。