(S)-5-(tert-Butyldiphenylsilyloxy)-4-hydroxypentan-2-one | 1552276-07-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (S)-5-(tert-Butyldiphenylsilyloxy)-4-hydroxypentan-2-one
• 英文别名: (4S)-5-[tert-butyl(diphenyl)silyl]oxy-4-hydroxypentan-2-one
• CAS: 1552276-07-9
• 化学式: C₂₁H₂₈O₃Si
• 分子量: 356.537
• InChiKey: RLFIDCHJHGJJHW-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (S)-5-(tert-Butyldiphenylsilyloxy)-4-hydroxypentan-2-one 在 (R)-3-(iodomethyl)-5,5-dimethoxy-2-methylpent-1-ene 、 四丁基氟化铵 、 三氧化硫吡啶 、 对甲苯磺酸 、 magnesium 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 6.08h， 生成 (5S,3Z)-4-hydroxy-5-((S)-2-hydroxy-2-methylbut-3-en-1-yl)-3-(iodomethylene)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Synthetic studies on polymaxenolides: model studies for constructing dihydropyran portion and synthesis of lower portion

  摘要：

  With a goal of the total synthesis of polymaxenolide, the first hybrid marine natural product, the model studies for constructing the dihydropyran portion based on the originally proposed biosynthesis (C-C bond formation followed by dehydrative cyclization) and the synthesis of the lower portion (the C1-C3, C7-C17 portion) based on an iodide-induced Morita-Baylis-Hillman type reaction (a three-component assembly) followed by Suzuki-Miyaura cross-coupling are described. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.076
• 作为产物：
  描述：

  1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-pent-4-en-2-ol 在 2,6-二甲基吡啶 、 四氧化锇 、 N-甲基吗啉氧化物 、 碘苯二乙酸 作用下， 以 水 、 丙酮 为溶剂， 反应 4.0h， 以55.2 g的产率得到(S)-5-(tert-Butyldiphenylsilyloxy)-4-hydroxypentan-2-one
  参考文献：
  名称：

  Synthetic studies on polymaxenolides: model studies for constructing dihydropyran portion and synthesis of lower portion

  摘要：

  With a goal of the total synthesis of polymaxenolide, the first hybrid marine natural product, the model studies for constructing the dihydropyran portion based on the originally proposed biosynthesis (C-C bond formation followed by dehydrative cyclization) and the synthesis of the lower portion (the C1-C3, C7-C17 portion) based on an iodide-induced Morita-Baylis-Hillman type reaction (a three-component assembly) followed by Suzuki-Miyaura cross-coupling are described. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.076

文献信息

• Synthetic studies on polymaxenolides: model studies for constructing dihydropyran portion and synthesis of lower portion
  作者：Yutaka Matsuda、Masaya Kato、Tomonori Kawaguchi、Takayuki Koyama、Yoko Saikawa、Masaya Nakata

  DOI：10.1016/j.tet.2013.12.076

  日期：2014.2

  With a goal of the total synthesis of polymaxenolide, the first hybrid marine natural product, the model studies for constructing the dihydropyran portion based on the originally proposed biosynthesis (C-C bond formation followed by dehydrative cyclization) and the synthesis of the lower portion (the C1-C3, C7-C17 portion) based on an iodide-induced Morita-Baylis-Hillman type reaction (a three-component assembly) followed by Suzuki-Miyaura cross-coupling are described. (C) 2014 Elsevier Ltd. All rights reserved.