(2R,3S)-2-(tert-butyldiphenylsilyl)oxy-3,4-epoxy-3-methylbutanal | 356787-10-5

• 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: (2R,3S)-2-(tert-butyldiphenylsilyl)oxy-3,4-epoxy-3-methylbutanal
• 英文别名: (2S)-2-[tert-butyl(diphenyl)silyl]oxy-2-[(2S)-2-methyloxiran-2-yl]acetaldehyde
• CAS: 356787-10-5
• 化学式: C₂₁H₂₆O₃Si
• 分子量: 354.521
• InChiKey: KVEAHSPZLPOVEU-CTNGQTDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-(tert-butyldiphenylsilyl)oxy-3,4-epoxy-3-methylbutanal 在 palladium diacetate 四丁基氟化铵 、 三正丁基氢锡 、 N,N-二异丙基乙胺 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 3.5h， 生成 (4E,6Z,2S,3R)-7-bromo-1,2-epoxy-2-methylhepta-4,6-dien-3-ol
  参考文献：
  名称：

  Asymmetric total synthesis of AK-toxins

  摘要：

  A practical total synthesis of AK-toxins (AK-toxin I, 1; II, 2), host-specific toxins against the Japanese pear, has been achieved in 10% total yield, starting from the key intermediate 6. The (2E,4Z,6E)-conjugated triene system was successfully constructed by the use of the Stille coupling reaction between the (E,Z)-bromodiene (17) and (E)-stannylacrylate (21). The (E,Z)-configuration of 17 was established with excellent geometrical purity by palladium-catalyzed stereoselective hydrogenolysis of gem-dibromide (15), which was derived from 6 via the Wittig-Horner reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00117-5
• 作为产物：
  描述：

  (R)-(3,3-dimethyloxiran-2-yl)methanol 在 咪唑 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 戴斯-马丁氧化剂 、 溶剂黄146 、 diisopropyl-d₀ D-tartrate 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 (2R,3S)-2-(tert-butyldiphenylsilyl)oxy-3,4-epoxy-3-methylbutanal
  参考文献：
  名称：

  Efficient stereoselective synthesis of a 1-hydroxymethyl-2-methylglycidol derivative

  摘要：

  A highly stereoselective synthesis of (2R.3S)-3,4-epoxy-3-methyl-1-(triphenylmethyl)oxybutan-2-ol 3, which is a substructure Found in some naturally-occurring bioactive compounds. was achieved starting from commercially available 3-methhyl-2-buten-1-ol 4 in three steps, using two applications of the Sharpless asymmetric epoxidation as the key stereochemistry establishing reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00149-5

文献信息

• Efficient stereoselective synthesis of a 1-hydroxymethyl-2-methylglycidol derivative
  作者：Ippei Uemura、Ken Yamada、Kayo Sugiura、Hisashi Miyagawa、Tamio Ueno

  DOI：10.1016/s0957-4166(01)00149-5

  日期：2001.4

  A highly stereoselective synthesis of (2R.3S)-3,4-epoxy-3-methyl-1-(triphenylmethyl)oxybutan-2-ol 3, which is a substructure Found in some naturally-occurring bioactive compounds. was achieved starting from commercially available 3-methhyl-2-buten-1-ol 4 in three steps, using two applications of the Sharpless asymmetric epoxidation as the key stereochemistry establishing reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Asymmetric total synthesis of AK-toxins
  作者：Ippei Uemura、Hisashi Miyagawa、Tamio Ueno

  DOI：10.1016/s0040-4020(02)00117-5

  日期：2002.3

  A practical total synthesis of AK-toxins (AK-toxin I, 1; II, 2), host-specific toxins against the Japanese pear, has been achieved in 10% total yield, starting from the key intermediate 6. The (2E,4Z,6E)-conjugated triene system was successfully constructed by the use of the Stille coupling reaction between the (E,Z)-bromodiene (17) and (E)-stannylacrylate (21). The (E,Z)-configuration of 17 was established with excellent geometrical purity by palladium-catalyzed stereoselective hydrogenolysis of gem-dibromide (15), which was derived from 6 via the Wittig-Horner reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.