(2R,4S)-5-azido-2,4-dimethylpentan-1-ol | 335060-50-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (2R,4S)-5-azido-2,4-dimethylpentan-1-ol
• CAS: 335060-50-9
• 化学式: C₇H₁₅N₃O
• 分子量: 157.216
• InChiKey: SOFQMAFMVYCFOO-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4S)-5-azido-2,4-dimethylpentan-1-ol 在 草酰氯 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (2R,3R)-5-[(2R,4S)-5-azido-4-methylpentan-2-yl]-5-methoxy-2-[(1S,3S)-1-[(4-methoxyphenyl)methoxy]-3-methylhex-5-ynyl]oxolan-3-ol
  参考文献：
  名称：

  Synthesis of the (+)-C26–C40 Domain of the Azaspiracids by a Novel Double Intramolecular Hetero-Michael Addition Strategy This work was supported by the United States National Institute of Environmental Health Sciences (NIEHS; grant number ES10615), NIH, and by Bristol-Myers Squibb (CJF). Its contents are solely the responsibility of the authors and do not necessarily represent the official views of the NIEHS, NIH, or BMS. We thank Dr. A. B. Dounay and Dr. G. Florence for critical reading of the manuscript.

  摘要：

  DOI：

  10.1002/1521-3773(20011001)40:19<3663::aid-anie3663>3.0.co;2-u
• 作为产物：
  描述：

  (2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol 在 叠氮磷酸二苯酯 、 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,4S)-5-azido-2,4-dimethylpentan-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.
• Synthesis of the (+)-C26–C40 Domain of the Azaspiracids by a Novel Double Intramolecular Hetero-Michael Addition Strategy This work was supported by the United States National Institute of Environmental Health Sciences (NIEHS; grant number ES10615), NIH, and by Bristol-Myers Squibb (CJF). Its contents are solely the responsibility of the authors and do not necessarily represent the official views of the NIEHS, NIH, or BMS. We thank Dr. A. B. Dounay and Dr. G. Florence for critical reading of the manuscript.
  作者：Craig J. Forsyth、Junliang Hao、Josep Aiguade

  DOI：10.1002/1521-3773(20011001)40:19<3663::aid-anie3663>3.0.co;2-u

  日期：2001.10.1