(2R,3S,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methyl-7-trimethylsilyl-6-heptynoic acid | 1196718-53-2

• 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: (2R,3S,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methyl-7-trimethylsilyl-6-heptynoic acid
• 英文别名: (2R,3S,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methyl-7-trimethylsilylhept-6-ynoic acid
• CAS: 1196718-53-2
• 化学式: C₂₃H₄₈O₄Si₃
• 分子量: 472.888
• InChiKey: VHGKLRAVAJUZPU-AQNXPRMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.76
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methyl-7-trimethylsilyl-6-heptynoic acid 在 氯甲酸乙酯 、 三乙胺 、 氨 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以86%的产率得到(2R,3S,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methyl-7-trimethylsilyl-6-heptynamide
  参考文献：
  名称：

  Stereoselective synthesis of the C1–C12 fragment of the thuggacins

  摘要：

  A concise asymmetric synthesis of the C1-C12 fragment of the antibacterial natural product thuggacins has been achieved. The stereochemistry of this fragment was established efficiently via stereoselective reduction and Evans-aldol condensation. Hanztsch's method and a Horner-Wadsworth-Emmnons reaction were employed for thiazole formation and the construction of the E-alpha,beta-unsaturated double bond. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.015
• 作为产物：
  描述：

  (R)-4-benzyl-3-[(S)-3-(R)-5-bis-(tert-butyl-dimethylsilanyloxy)-(R)-2-methyl-7-trimethylsilyl-hept-6-ynoyl]-oxazolidin-2-one 在 双氧水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以74%的产率得到(2R,3S,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methyl-7-trimethylsilyl-6-heptynoic acid
  参考文献：
  名称：

  Stereoselective synthesis of the C1–C12 fragment of the thuggacins

  摘要：

  A concise asymmetric synthesis of the C1-C12 fragment of the antibacterial natural product thuggacins has been achieved. The stereochemistry of this fragment was established efficiently via stereoselective reduction and Evans-aldol condensation. Hanztsch's method and a Horner-Wadsworth-Emmnons reaction were employed for thiazole formation and the construction of the E-alpha,beta-unsaturated double bond. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.015

文献信息

• Stereoselective synthesis of the C1–C12 fragment of the thuggacins
  作者：Shoubin Tang、Zhengshuang Xu、Tao Ye

  DOI：10.1016/j.tetasy.2009.08.015

  日期：2009.9

  A concise asymmetric synthesis of the C1-C12 fragment of the antibacterial natural product thuggacins has been achieved. The stereochemistry of this fragment was established efficiently via stereoselective reduction and Evans-aldol condensation. Hanztsch's method and a Horner-Wadsworth-Emmnons reaction were employed for thiazole formation and the construction of the E-alpha,beta-unsaturated double bond. (C) 2009 Elsevier Ltd. All rights reserved.