methyl (E)-(5S,6R,7R,8S)-5-[tert-butyl(dimethyl)silyl]oxy-7-methoxy-2,6,8-trimethyldec-2-enoate | 1538576-02-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl (E)-(5S,6R,7R,8S)-5-[tert-butyl(dimethyl)silyl]oxy-7-methoxy-2,6,8-trimethyldec-2-enoate
• 英文别名: methyl (E,5S,6R,7R,8S)-5-[tert-butyl(dimethyl)silyl]oxy-7-methoxy-2,6,8-trimethyldec-2-enoate
• CAS: 1538576-02-1
• 化学式: C₂₁H₄₂O₄Si
• 分子量: 386.648
• InChiKey: SNWAELIWDVXHPQ-HTJXHCOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-(5S,6R,7R,8S)-5-[tert-butyl(dimethyl)silyl]oxy-7-methoxy-2,6,8-trimethyldec-2-enoate 在 potassium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 72.0h， 以97%的产率得到(E)-(5S,6R,7R,8S)-5-[tert-butyl(dimethyl)silyl]oxy-7-methoxy-2,6,8-trimethyl-dec-2-enoic acid
  参考文献：
  名称：

  An efficient synthesis of the C27–C45 fragment of lagunamide A, a cyclodepsipeptide with potent cytotoxic and antimalarial properties

  摘要：

  An efficient and stereoselective synthesis of the entire C27-C45 moiety of lagunamide A has been achieved from 1-[(4S)-4-benzyl-2-thioxothiazolidin-3-yl]propan-1-one in six steps with 22% overall yield. The key step in the synthesis is an asymmetric acetal aldol reaction featuring the enantioselective addition of a chiral thiazolidinethione-derived titanium enolate to an acetal to establish the stereochemistry at C39. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.11.020
• 作为产物：
  描述：

  (S)-1,1-dimethoxy-2-methylbutane 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 四氯化钛 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.42h， 生成 methyl (E)-(5S,6R,7R,8S)-5-[tert-butyl(dimethyl)silyl]oxy-7-methoxy-2,6,8-trimethyldec-2-enoate
  参考文献：
  名称：

  An efficient synthesis of the C27–C45 fragment of lagunamide A, a cyclodepsipeptide with potent cytotoxic and antimalarial properties

  摘要：

  An efficient and stereoselective synthesis of the entire C27-C45 moiety of lagunamide A has been achieved from 1-[(4S)-4-benzyl-2-thioxothiazolidin-3-yl]propan-1-one in six steps with 22% overall yield. The key step in the synthesis is an asymmetric acetal aldol reaction featuring the enantioselective addition of a chiral thiazolidinethione-derived titanium enolate to an acetal to establish the stereochemistry at C39. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.11.020

文献信息

• An efficient synthesis of the C27–C45 fragment of lagunamide A, a cyclodepsipeptide with potent cytotoxic and antimalarial properties
  作者：Hui-Ming Liu、Chieh-Yu Chang、Ya-Chi Lai、Mei-Due Yang、Ching-Yao Chang

  DOI：10.1016/j.tetasy.2013.11.020

  日期：2014.1

  An efficient and stereoselective synthesis of the entire C27-C45 moiety of lagunamide A has been achieved from 1-[(4S)-4-benzyl-2-thioxothiazolidin-3-yl]propan-1-one in six steps with 22% overall yield. The key step in the synthesis is an asymmetric acetal aldol reaction featuring the enantioselective addition of a chiral thiazolidinethione-derived titanium enolate to an acetal to establish the stereochemistry at C39. (C) 2013 Elsevier Ltd. All rights reserved.