(3R,4S)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-3-ethyl-2-azetidinone | 143658-95-1

• 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,4S)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-3-ethyl-2-azetidinone
• 英文别名: (3R,4S)-4-((4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl)-1-p-methoxyphenyl-3-ethyl-2-azetidinone；(3R,4S)-4-[(4S,5S)-4,5-bis(methoxymethyl)-2-methyl-1,3-dioxolan-2-yl]-3-ethyl-1-(4-methoxyphenyl)azetidin-2-one
• CAS: 143658-95-1
• 化学式: C₂₀H₂₉NO₆
• 分子量: 379.453
• InChiKey: LTDKYVPISOZJTR-OWSLCNJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4S)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-3-ethyl-2-azetidinone 生成 (3R,4R)-3-乙基-4-乙酰氧基-2-氮杂环丁酮
  参考文献：
  名称：

  A stereocontrolled method for the synthesis of each of the four diastereomers of 34-dialkyl-substituted β-lactams using different metal ester enolates and a chiral imine

  摘要：

  The reaction of the different metal ester enolates of t-butyl alpha-alkyl substituted acetates with a chiral imine possessing a dioxolane ring derived from (2S,3S)-1,4-dimethoxy-2,3-butanediol as a chiral auxiliary followed by cyclization of the initial products of beta-amino esters gave each of the diastereomers of 3,4-dialkyl-substituted beta-lactams in a highly stereoselective manner, i.e., the titanium enolate gave trans-(3R,4S)-isomer, while the lithium and zinc ones afforded cis-(3S,4S)- and (3R,4R)-isomers, respectively, and the cis-(3R,4R)-beta-lactams thus obtained were readily epimerized to the corresponding trans-(3S,4R)-beta-lactams without loss of the stereochemical integrity at C4.

  DOI：

  10.1016/s0040-4039(00)91781-7
• 作为产物：
  描述：

  (4S,5S)-4,5-dimethoxymethyl-2-(N-p-methoxyphenyl)iminomethyl-2-methyl-1,3-dioxolane 在 lithium diisopropyl amide 作用下， 反应 1.5h， 生成 (3R,4S)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-3-ethyl-2-azetidinone
  参考文献：
  名称：

  锂或钛酸酯烯酸酯与手性亚胺的非对映异构反应导致β-内酰胺的立体发散合成

  摘要：

  据报道，酯烯酸酯与具有（4 S，5 S）-4,5-二甲氧基甲基-2-甲基-1,3-二氧戊环作为手性助剂的手性亚胺的非对映选择性加成反应，其中各种金属烯酸酯导致选择性形成（4 S）-或（4 R）-β-内酰胺。即，添加烯醇锂提供了（4 S）-β-内酰胺，而三异丙氧基钛烯醇盐实现了选择性形成（4 R）-β-内酰胺，证明了一个成功的例子，其中钛酸酯烯醇盐用于与亚胺。可能的中间体导致（4 S）-和（4 R还讨论了异构体，并假定了钛和锂金属与手性助剂的不同配位能力以反映选择性的逆转。

  DOI：

  10.1016/0040-4020(92)80013-6

文献信息

• Diastereoface-discrimination reaction of lithium or titanium ester enolates with a chiral imine leading to stereodivergent synthesis of β-lactams
  作者：Tamotsu Fujisawa、Yutaka Ukaji、Tomohiro Noro、Kengo Date、Makoto Shimizu

  DOI：10.1016/0040-4020(92)80013-6

  日期：1992.7

  Diastereoselective addition reaction of ester enolates to a chiral imine possessing (4S, 5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolane ring as a chiral auxiliary is reported, in which varying metal enolates resulted in the selective formation of (4S)- or (4R)-β-lactam. Namely, addition of the lithium enolates provided (4S)-β-lactams, whereas the triisopropoxytitanium enolates effected selective formation

  据报道，酯烯酸酯与具有（4 S，5 S）-4,5-二甲氧基甲基-2-甲基-1,3-二氧戊环作为手性助剂的手性亚胺的非对映选择性加成反应，其中各种金属烯酸酯导致选择性形成（4 S）-或（4 R）-β-内酰胺。即，添加烯醇锂提供了（4 S）-β-内酰胺，而三异丙氧基钛烯醇盐实现了选择性形成（4 R）-β-内酰胺，证明了一个成功的例子，其中钛酸酯烯醇盐用于与亚胺。可能的中间体导致（4 S）-和（4 R还讨论了异构体，并假定了钛和锂金属与手性助剂的不同配位能力以反映选择性的逆转。
• A stereocontrolled method for the synthesis of each of the four diastereomers of 34-dialkyl-substituted β-lactams using different metal ester enolates and a chiral imine
  作者：Tamotsu Fujisawa、Mitsuhiro Ichikawa、Yutaka Ukaji、Makoto Shimizu

  DOI：10.1016/s0040-4039(00)91781-7

  日期：1993.2

  The reaction of the different metal ester enolates of t-butyl alpha-alkyl substituted acetates with a chiral imine possessing a dioxolane ring derived from (2S,3S)-1,4-dimethoxy-2,3-butanediol as a chiral auxiliary followed by cyclization of the initial products of beta-amino esters gave each of the diastereomers of 3,4-dialkyl-substituted beta-lactams in a highly stereoselective manner, i.e., the titanium enolate gave trans-(3R,4S)-isomer, while the lithium and zinc ones afforded cis-(3S,4S)- and (3R,4R)-isomers, respectively, and the cis-(3R,4R)-beta-lactams thus obtained were readily epimerized to the corresponding trans-(3S,4R)-beta-lactams without loss of the stereochemical integrity at C4.