(2R,4S)-4-[(4S)-2,2-dimethyl-5-methylidene-1,3-dioxan-4-yl]-2-methylpentan-1-ol | 335060-61-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4S)-4-[(4S)-2,2-dimethyl-5-methylidene-1,3-dioxan-4-yl]-2-methylpentan-1-ol
• CAS: 335060-61-2
• 化学式: C₁₃H₂₄O₃
• 分子量: 228.332
• InChiKey: KGQHXWWLFWEMKK-SCVCMEIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4S)-4-[(4S)-2,2-dimethyl-5-methylidene-1,3-dioxan-4-yl]-2-methylpentan-1-ol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 indium 、 sodium chlorite 、 N-溴代丁二酰亚胺(NBS) 、 氯化铵 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 phosphate buffer 、 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Remarkably chemoselective indium-mediated coupling en route to the C21–C40 acyclic portion of the azaspiracids

  摘要：

  A densely functionalized acyclic intermediate representing the C21-C40 portion of the novel marine natural product azaspiracid was prepared via a chemoselective indium-mediated coupling between C21-C27 and C28-C40 intermediates. Although the coupling partners contained aldehyde, azide, ketone, enone, and lactone functionalities. the C21-C27 allylic species added selectively to the aldehyde of a C28-C40 intermediate under aqueous indium-mediated conditions. The C21-C27 and C35-C40 fragments were prepared in a divergent fashion from a common syn-1,3-dimethyl synthon 9. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02157-2
• 作为产物：
  描述：

  (2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 生成 (2R,4S)-4-[(4S)-2,2-dimethyl-5-methylidene-1,3-dioxan-4-yl]-2-methylpentan-1-ol
  参考文献：
  名称：

  Remarkably chemoselective indium-mediated coupling en route to the C21–C40 acyclic portion of the azaspiracids

  摘要：

  A densely functionalized acyclic intermediate representing the C21-C40 portion of the novel marine natural product azaspiracid was prepared via a chemoselective indium-mediated coupling between C21-C27 and C28-C40 intermediates. Although the coupling partners contained aldehyde, azide, ketone, enone, and lactone functionalities. the C21-C27 allylic species added selectively to the aldehyde of a C28-C40 intermediate under aqueous indium-mediated conditions. The C21-C27 and C35-C40 fragments were prepared in a divergent fashion from a common syn-1,3-dimethyl synthon 9. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02157-2

文献信息

• Remarkably chemoselective indium-mediated coupling en route to the C21–C40 acyclic portion of the azaspiracids
  作者：Junliang Hao、Josep Aiguade、Craig J Forsyth

  DOI：10.1016/s0040-4039(00)02157-2

  日期：2001.1

  A densely functionalized acyclic intermediate representing the C21-C40 portion of the novel marine natural product azaspiracid was prepared via a chemoselective indium-mediated coupling between C21-C27 and C28-C40 intermediates. Although the coupling partners contained aldehyde, azide, ketone, enone, and lactone functionalities. the C21-C27 allylic species added selectively to the aldehyde of a C28-C40 intermediate under aqueous indium-mediated conditions. The C21-C27 and C35-C40 fragments were prepared in a divergent fashion from a common syn-1,3-dimethyl synthon 9. (C) 2001 Elsevier Science Ltd. All rights reserved.