methyl (3R)-4-[1-(tert-butyl)-1,1-dimethylsilyloxy]oxy-3-(1-ethoxy-2-methylallylox)butanoate | 1013918-23-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (3R)-4-[1-(tert-butyl)-1,1-dimethylsilyloxy]oxy-3-(1-ethoxy-2-methylallylox)butanoate
• 英文别名: methyl (3R)-4-[tert-butyl(dimethyl)silyl]oxy-3-(1-ethoxy-2-methylprop-2-enoxy)butanoate
• CAS: 1013918-23-4
• 化学式: C₁₇H₃₄O₅Si
• 分子量: 346.539
• InChiKey: XHFCASIKCXRNEX-IURRXHLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,1-diethoxy-2-methyl-2-propene 、 methyl (R)-4-(tert-butyldimethylsilyloxy)-3-hydroxybutanoate 在 4-甲基苯磺酸吡啶 作用下， 以 甲苯 为溶剂， 20.0 ℃ 、5.5 kPa 条件下， 反应 24.0h， 以49%的产率得到methyl (3R)-4-[1-(tert-butyl)-1,1-dimethylsilyloxy]oxy-3-(1-ethoxy-2-methylallylox)butanoate
  参考文献：
  名称：

  Metathesis-based synthesis of 3-methoxy α,β-unsaturated lactones: total synthesis of (R)-kavain and of the C1–C6 fragment of jerangolid D

  摘要：

  The total synthesis of (R)-kavain and of the C1-C6 fragment of jerangolid D has been achieved in nine and seven steps, respectively, from commercially available dimethyl D-Malate. A metathesis reaction of vinyl ethers and a sulfoxide-modified Julia olefination have been employed as the key steps. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.12.113

文献信息

• Metathesis-based synthesis of 3-methoxy α,β-unsaturated lactones: total synthesis of (R)-kavain and of the C1–C6 fragment of jerangolid D
  作者：Jiří Pospíšil、István E. Markó

  DOI：10.1016/j.tetlet.2007.12.113

  日期：2008.2

  The total synthesis of (R)-kavain and of the C1-C6 fragment of jerangolid D has been achieved in nine and seven steps, respectively, from commercially available dimethyl D-Malate. A metathesis reaction of vinyl ethers and a sulfoxide-modified Julia olefination have been employed as the key steps. (c) 2007 Elsevier Ltd. All rights reserved.