2,3-O-isopropylidene-γ-D-ribonolactone acetoacetate | 89747-52-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 2,3-O-isopropylidene-γ-D-ribonolactone acetoacetate
• 英文别名: [(3aR,6R,6aR)-2,2-dimethyl-4-oxo-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-6-yl]methyl 3-oxobutanoate
• CAS: 89747-52-4
• 化学式: C₁₂H₁₆O₇
• 分子量: 272.255
• InChiKey: ODTDKRKRZRLDLF-SZEHBUNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3-O-isopropylidene-γ-D-ribonolactone acetoacetate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 36.5h， 生成 2,3-O-isopropylidene-γ-D-ribonolactone (2R)-2-butyl-(2-naphthylmethyl)acetoacetate
  参考文献：
  名称：

  Asymmetric synthesis of quaternary α-amino acids using d-ribonolactone acetonide as chiral auxiliary

  摘要：

  We describe a new simple methodology to prepare enantiopure alpha,alpha-dialkylglycines based on the use of commercially available D-ribonolactone as a chiral auxiliary. Enantiopure alpha-methyl and alpha-butyl series are prepared through diastereoselective alkylation and subsequent Schmidt rearrangement of alpha,alpha-dialkylacetoacetates of D-ribonolactone acetonide. Absolute configuration was assigned through preparation of enantiopure 4,4-disubstituted 3-methyl-2-pyrazolin-5-ones. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00457-7
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 、 2,2,6-三甲基-4H-1,3-二英-4-酮 以 甲苯 为溶剂， 反应 24.0h， 以82%的产率得到2,3-O-isopropylidene-γ-D-ribonolactone acetoacetate
  参考文献：
  名称：

  Asymmetric synthesis of quaternary α-amino acids using d-ribonolactone acetonide as chiral auxiliary

  摘要：

  We describe a new simple methodology to prepare enantiopure alpha,alpha-dialkylglycines based on the use of commercially available D-ribonolactone as a chiral auxiliary. Enantiopure alpha-methyl and alpha-butyl series are prepared through diastereoselective alkylation and subsequent Schmidt rearrangement of alpha,alpha-dialkylacetoacetates of D-ribonolactone acetonide. Absolute configuration was assigned through preparation of enantiopure 4,4-disubstituted 3-methyl-2-pyrazolin-5-ones. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00457-7

文献信息

• Inhibition of arabinose 5-phosphate isomerase. An approach to the inhibition of bacterial lipopolysaccharide biosynthesis
  作者：Eric C. Bigham、Charles E. Gragg、William R. Hall、John E. Kelsey、William R. Mallory、Drew C. Richardson、Charles Benedict、Paul H. Ray

  DOI：10.1021/jm00372a003

  日期：1984.6

  Arabinose 5-phosphate ( A5P ) isomerase is a key enzyme in the biosynthesis of lipopolysaccharide, an essential component of the outer membrane of Gram-negative bacteria. The mechanism of the isomerase is envisioned to involve an enediol intermediate. A series of compounds, which are analogues of the substrates or intermediate, were tested as inhibitors of A5P isomerase with the belief that a good

  5-磷酸阿拉伯糖（A5P）异构酶是脂多糖生物合成中的关键酶，脂多糖是革兰氏阴性细菌外膜的重要组成部分。设想异构酶的机理涉及烯二醇中间体。测试了一系列与底物或中间体类似的化合物作为A5P异构酶的抑制剂，并认为良好的抑制剂会阻止细菌生长或使细胞更易受其他抗生素或自然防御作用。在一系列磷酸化糖中，异构酶抑制活性的顺序如下：醛糖酸大于醛糖醇大于醛糖。非磷酸化糖的抑制作用要小得多。最好的抑制剂是4-磷酸赤藓酸（54），Km / Ki = 29。
• Electrochemically-initiated Michael addition of chiral acetoacetic derivatives to methyl vinyl ketone: stereocontrolled construction of quaternary carbon centers
  作者：Laura Palombi、Marta Feroci、Monica Orsini、Achille Inesi

  DOI：10.1016/s0957-4166(02)00636-5

  日期：2002.10

  Stereoselective conjugate addition of chiral β-dicarbonyl derivatives to methyl vinyl ketone was promoted by electrolysis, using a catalytic amount of electricity. With respect to the metal-catalyzed methods, the electrochemical, metal-free conditions resulted in enhanced reactivity of the electrogenerated enolates, so that the Michael addition was found to occur under mild conditions and short reaction

  通过催化作用，利用催化量的电，手性β-二羰基衍生物向甲基乙烯基酮的立体选择性共轭加成反应。关于金属催化的方法，电化学，无金属的条件导致电生成的烯醇化物的反应性增强，因此发现迈克尔加成反应在温和的条件下和较短的反应时间下进行，从而提供了具有明显非对映异构体过量的产物。当将Oppolzer的sultam用作手性诱导剂并使用延长的反应时间时，观察到立体选择性的逆转，证明了电化学诱导的加成反应和随后的热力学平衡的动力学控制。基于电化学的方法也被用于精制季生立体碳中心。
• MINASKANIAN, GEVORK
  作者：MINASKANIAN, GEVORK

  DOI：——

  日期：——