(2R)-2,3-dihydroxypropanoic acid β-trimethylsilylethyl ester | 862546-75-6

• 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: (2R)-2,3-dihydroxypropanoic acid β-trimethylsilylethyl ester
• CAS: 862546-75-6
• 化学式: C₈H₁₈O₄Si
• 分子量: 206.314
• InChiKey: XDKKSLYEIDLJRZ-SSDOTTSWSA-N

物化性质

• 沸点：
  292.0±19.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.22
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R)-2,3-dihydroxypropanoic acid β-trimethylsilylethyl ester 、 (三苯基膦烯)乙烯酮 、 棕榈酸 以26%的产率得到3-十六烷酰基-5-羟甲基tetronic酸
  参考文献：
  名称：

  Solution-Phase and Solid-Phase Syntheses of Enzyme Inhibitor RK-682 and Antibiotic Agglomerins

  摘要：

  The enzyme inhibitor RK-682 (5R)-(+)-1 was prepared in solution and on a solid support from (2R)-glycerates in five steps and ca. 40% overall yield. Key steps were a ring-closing tandem addition-Wittig alkenation reaction of the respective protected or immobilized glycerates with the ylide Ph-3-PCCO and the 3-acylation of the tetronic acids thus obtained with palmitic acid. A similar route extended by a mesylation-elimination sequence led to antibiotic agglomerins A-C 2 featuring 3-acyl-5-methylidenetetronic acid structures.

  DOI：

  10.1021/jo050797i
• 作为产物：
  描述：

  N.N'-Dicyclohexyl-O-(2-trimethylsilyl-aethyl)-isoharnstoff 在 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 (2R)-2,3-dihydroxypropanoic acid β-trimethylsilylethyl ester
  参考文献：
  名称：

  Solution-Phase and Solid-Phase Syntheses of Enzyme Inhibitor RK-682 and Antibiotic Agglomerins

  摘要：

  The enzyme inhibitor RK-682 (5R)-(+)-1 was prepared in solution and on a solid support from (2R)-glycerates in five steps and ca. 40% overall yield. Key steps were a ring-closing tandem addition-Wittig alkenation reaction of the respective protected or immobilized glycerates with the ylide Ph-3-PCCO and the 3-acylation of the tetronic acids thus obtained with palmitic acid. A similar route extended by a mesylation-elimination sequence led to antibiotic agglomerins A-C 2 featuring 3-acyl-5-methylidenetetronic acid structures.

  DOI：

  10.1021/jo050797i