(E)-(2R,3S)-2-Benzyloxy-2-methyl-hex-4-ene-1,3-diol | 366494-36-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-(2R,3S)-2-Benzyloxy-2-methyl-hex-4-ene-1,3-diol
• 英文别名: (E,2R,3S)-2-methyl-2-phenylmethoxyhex-4-ene-1,3-diol
• CAS: 366494-36-2
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: NPJPAJJAVPXVRW-VTBFOEKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-(2R,3S)-2-Benzyloxy-2-methyl-hex-4-ene-1,3-diol 在 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 tert-Butyl-dimethyl-[(4R,5S)-2,2,4-trimethyl-5-((E)-propenyl)-[1,3]dioxolan-4-ylmethoxy]-silane
  参考文献：
  名称：

  Stereocontrolled preparation of 1,2-diol with quaternary chiral center

  摘要：

  Development of an enantio- and stereoselective construction of 1,2-diols including a quaternary chiral center was achieved by a titanium-mediated aldol reaction of lactates bearing chiral oxazolidine-2-ones. anti-Aldol and syn-aldol were selectively obtained by the choice of a benzyl and TBS protecting group, respectively. Plausible transition states are also shown based on the stereochemistry of the enolate anion. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01946-9
• 作为产物：
  描述：

  苯甲醇 、 (4S)-3-[(E,2S,3S)-3-hydroxy-2-methyl-2-phenylmethoxyhex-4-enoyl]-5,5-dimethyl-4-propan-2-yl-1,3-oxazolidin-2-one 在 正丁基锂 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-(2R,3S)-2-Benzyloxy-2-methyl-hex-4-ene-1,3-diol
  参考文献：
  名称：

  Stereocontrolled preparation of 1,2-diol with quaternary chiral center

  摘要：

  Development of an enantio- and stereoselective construction of 1,2-diols including a quaternary chiral center was achieved by a titanium-mediated aldol reaction of lactates bearing chiral oxazolidine-2-ones. anti-Aldol and syn-aldol were selectively obtained by the choice of a benzyl and TBS protecting group, respectively. Plausible transition states are also shown based on the stereochemistry of the enolate anion. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01946-9

文献信息

• Total Synthesis of Incednam, the Aglycon of Incednine
  作者：Takashi Ohtani、Shinya Tsukamoto、Hiroshi Kanda、Kensuke Misawa、Yoshifumi Urakawa、Takahiro Fujimaki、Masaya Imoto、Yoshikazu Takahashi、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1021/ol102400c

  日期：2010.11.5

  The first total synthesis of incednam (1), the aglycon of antibiotic incednine (2), is described. Incednine has been reported to exhibit significant inhibitory activity against the antiapoptotic oncoproteins Bcl-2 and Bcl-xL. The synthesis of 1 commenced with the preparation of the C1−C13 subunit 3 and the C14−C23 subunit 4. The construction of the novel 24-membered macrocycle was achieved by the application

  描述了incednam（1）的第一个全合成，即抗生素incednine（2）的糖苷配基。据报道，Incednine对抗凋亡的癌蛋白Bcl-2和Bcl-xL表现出显着的抑制活性。1的合成从C1-C13亚基3和C14-C23亚基4的制备开始。通过在3和4之间应用Stille偶联，然后进行内酰胺化，可实现新型24元大环化合物的构建。