(E,4R,6R)-6-[(4S,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]-2,4-dimethylhept-2-en-1-ol | 1242057-58-4

• 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,4R,6R)-6-[(4S,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]-2,4-dimethylhept-2-en-1-ol
• CAS: 1242057-58-4
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: IMIDYTAAPTZSSC-ZFCJFZHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E,4R,6R)-6-[(4S,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]-2,4-dimethylhept-2-en-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 D-(-)-酒石酸二乙酯 作用下， 反应 12.0h， 以84%的产率得到[(2R,3R)-3-[(2R,4R)-4-[(4S,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]pentan-2-yl]-2-methyloxiran-2-yl]methanol
  参考文献：
  名称：

  Synthesis of C15–C27 segment of venturicidine X by utilizing desymmetrization protocol

  摘要：

  We have achieved the synthesis of C15-C27 fragment of venturicidine X using desymmetrization protocol, substrate-controlled Grignard reaction, Barton-McCombie reaction, Sharpless epoxidation, and TBSOTf-mediated rearrangement to produce the aldol product through a non-aldol route as the key step following 23 longest linear sequences with 6.4% overall yield starting from a known intermediate 11. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.148
• 作为产物：
  描述：

  ethyl (E,4R,6R)-6-[(4S,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]-2,4-dimethylhept-2-enoate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到(E,4R,6R)-6-[(4S,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]-2,4-dimethylhept-2-en-1-ol
  参考文献：
  名称：

  Synthesis of C15–C27 segment of venturicidine X by utilizing desymmetrization protocol

  摘要：

  We have achieved the synthesis of C15-C27 fragment of venturicidine X using desymmetrization protocol, substrate-controlled Grignard reaction, Barton-McCombie reaction, Sharpless epoxidation, and TBSOTf-mediated rearrangement to produce the aldol product through a non-aldol route as the key step following 23 longest linear sequences with 6.4% overall yield starting from a known intermediate 11. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.148

文献信息

• Synthesis of C15–C27 segment of venturicidine X by utilizing desymmetrization protocol
  作者：J.S. Yadav、Sk. Samad Hossain、Debendra K. Mohapatra

  DOI：10.1016/j.tetlet.2010.05.148

  日期：2010.8

  We have achieved the synthesis of C15-C27 fragment of venturicidine X using desymmetrization protocol, substrate-controlled Grignard reaction, Barton-McCombie reaction, Sharpless epoxidation, and TBSOTf-mediated rearrangement to produce the aldol product through a non-aldol route as the key step following 23 longest linear sequences with 6.4% overall yield starting from a known intermediate 11. (C) 2010 Elsevier Ltd. All rights reserved.