(R)-erythrulose triacetate | 78215-66-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-erythrulose triacetate
• 英文别名: [(2R)-2,4-diacetyloxy-3-oxobutyl] acetate
• CAS: 78215-66-4
• 化学式: C₁₀H₁₄O₇
• 分子量: 246.217
• InChiKey: OZELUSIWJMWFMD-SNVBAGLBSA-N

物化性质

• 沸点：
  332.5±42.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  D-(-)-苏糖 生成 (R)-erythrulose triacetate
  参考文献：
  名称：

  Formation of 3-octuloses by a self-aldol reaction of d-erythrose

  摘要：

  DOI：

  10.1016/s0008-6215(00)80987-8

文献信息

• Chemoselective Pd-Catalyzed Oxidation of Polyols: Synthetic Scope and Mechanistic Studies
  作者：Kevin Chung、Steven M. Banik、Antonio G. De Crisci、David M. Pearson、Timothy R. Blake、Johan V. Olsson、Andrew J. Ingram、Richard N. Zare、Robert M. Waymouth

  DOI：10.1021/ja4008694

  日期：2013.5.22

  9-dimethyl-1,10-phenanthroline) occurs readily under mild reaction conditions to generate α-hydroxy ketones. The oxidation of vicinal diols is both faster and more selective than the oxidation of primary and secondary alcohols; vicinal 1,2-diols are oxidized selectively to hydroxy ketones, whereas primary alcohols are oxidized in preference to secondary alcohols. Oxidative lactonization of 1,5-diols yields

  在温和的反应条件下，未保护的邻位多元醇与 [(neocuproine)Pd(OAc)]2(OTf)2 (1)（neocuproine = 2,9-二甲基-1,10-菲咯啉）的区域和化学选择性氧化很容易发生生成α-羟基酮。邻二醇的氧化比伯醇和仲醇的氧化速度更快，选择性更强；邻位 1,2-二醇被选择性氧化为羟基酮，而伯醇优先于仲醇氧化。1,5-二醇的氧化内酯化产生环内酯。在 10 克规模的氧化反应中，可以使用低至 0.12 mol% 的催化剂负载量。在多元醇 (S,S)-1,2,3,4-四羟基丁烷 [(S,S)-苏糖醇] 到 (S)-赤藓酮糖的化学选择性和立体定向氧化过程中，该催化剂体系的卓越选择性是显而易见的。机械的，动力学和理论研究表明，伯醇和仲醇的氧化速率定律与二醇不同。密度泛函理论计算支持以下结论：β-氢化物消除产生羟基酮是邻二醇氧化的产物决定因素，而对于伯醇和仲醇，有利于伯醇盐的预平
• Chemoselective Oxidation of Polyols with Chiral Palladium Catalysts
  作者：Antonio G. De Crisci、Kevin Chung、Allen G. Oliver、Diego Solis-Ibarra、Robert M. Waymouth

  DOI：10.1021/om4001549

  日期：2013.4.8

  Chiral palladium-based catalysts derived from pyridinyl oxazoline (pyOx) ligands catalyze the oxidation of alcohols, including 1,2-diols, triols, and tetraols, with high regio- and chemoselectivity. Screening of various chiral oxazoline-derived ligands for the oxidation of a model diol, 1,2-propanediol (1,2-PD), revealed that the nature of the ligand had a significant influence on the activity and cliemoselectivity for oxidation of vicinal diols. The PyOx ligands containing an a-methyl substituent were the most active for the oxidation of 1,2-PD using benzoquinone as the terminal oxidant. Oxidation of vicinal diols and polyols occurs selectively at the secondary alcohol to afford a-hydroxy ketones in isolated yields of 62-87%. Chemoselective oxidation of meso-erythritol with the chiral [(S)-(alpha-Me(tert-Bu)PyOx)Pd(OAc)](2)[OTf](2) afforded (S)-erthyrulose in 62% yield and 24%
• Formation of 3-octuloses by a self-aldol reaction of d-erythrose
  作者：Eric Westerlund

  DOI：10.1016/s0008-6215(00)80987-8

  日期：1981.4