2-methylpropyl (2R,3R)-3-hydroxy-2-methylhex-5-enoate | 1246920-54-6

• 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: 2-methylpropyl (2R,3R)-3-hydroxy-2-methylhex-5-enoate
• CAS: 1246920-54-6
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: XJZQYKRWUKOGEH-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methylpropyl (2R,3R)-3-hydroxy-2-methylhex-5-enoate 、 三乙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到isobutyl (2R,3R)-2-methyl-3-((triethylsilyl)oxy)hex-5-enoate
  参考文献：
  名称：

  Enantioselective Total Synthesis of Spirofungins A and B

  摘要：

  The enantioselective total synthesis of spirofungins A (1) and B (2) is reported in 14 steps over the longest linear sequence. Key steps include the use of thiazolidinethione-mediated aldol reactions to assemble the major fragments and installation of the C1-C6 side chain using a cross metathesis reaction.

  DOI：

  10.1021/ol101961c
• 作为产物：
  描述：

  isobutyl (R)-3-hydroxyhex-5-enoate 、 碘甲烷 在 正丁基锂 、 二异丙胺 、 N,N-二甲基丙烯基脲 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以63%的产率得到2-methylpropyl (2R,3R)-3-hydroxy-2-methylhex-5-enoate
  参考文献：
  名称：

  Enantioselective Total Synthesis of Spirofungins A and B

  摘要：

  The enantioselective total synthesis of spirofungins A (1) and B (2) is reported in 14 steps over the longest linear sequence. Key steps include the use of thiazolidinethione-mediated aldol reactions to assemble the major fragments and installation of the C1-C6 side chain using a cross metathesis reaction.

  DOI：

  10.1021/ol101961c

文献信息

• Enantioselective Total Synthesis of Spirofungins A and B
  作者：Michael T. Crimmins、Elizabeth A. O’Bryan

  DOI：10.1021/ol101961c

  日期：2010.10.1

  The enantioselective total synthesis of spirofungins A (1) and B (2) is reported in 14 steps over the longest linear sequence. Key steps include the use of thiazolidinethione-mediated aldol reactions to assemble the major fragments and installation of the C1-C6 side chain using a cross metathesis reaction.