tert-Butyl-[(2R,4S)-4-((S)-2,2-dimethyl-5-methylene-[1,3]dioxan-4-yl)-2-methyl-pentyloxy]-dimethyl-silane | 335060-52-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl-[(2R,4S)-4-((S)-2,2-dimethyl-5-methylene-[1,3]dioxan-4-yl)-2-methyl-pentyloxy]-dimethyl-silane
• CAS: 335060-52-1
• 化学式: C₁₉H₃₈O₃Si
• 分子量: 342.594
• InChiKey: VQXMNRMIJKKQCH-VYDXJSESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-Butyl-[(2R,4S)-4-((S)-2,2-dimethyl-5-methylene-[1,3]dioxan-4-yl)-2-methyl-pentyloxy]-dimethyl-silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到(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
• 作为产物：
  描述：

  (E)-(4S,6R)-7-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-hept-2-enoic acid ethyl ester 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 、 camphor-10-sulfonic acid 、 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 tert-Butyl-[(2R,4S)-4-((S)-2,2-dimethyl-5-methylene-[1,3]dioxan-4-yl)-2-methyl-pentyloxy]-dimethyl-silane
  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