(4R)-4-(2'-trimethylsilylethoxycarbonyl)-2,2-dimethyl-1,3-dioxolane | 862546-74-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R)-4-(2'-trimethylsilylethoxycarbonyl)-2,2-dimethyl-1,3-dioxolane
• CAS: 862546-74-5
• 化学式: C₁₁H₂₂O₄Si
• 分子量: 246.379
• InChiKey: AEIJUGCYAMZGAO-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4R)-4-(2'-trimethylsilylethoxycarbonyl)-2,2-dimethyl-1,3-dioxolane 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 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
• 作为产物：
  描述：

  (4R)-4-benzyloxycarbonyl-2,2-dimethyl-1,3-dioxolane 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 20.0~50.0 ℃ 、100.0 kPa 条件下， 反应 13.0h， 生成 (4R)-4-(2'-trimethylsilylethoxycarbonyl)-2,2-dimethyl-1,3-dioxolane
  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