ethyl (6E,2S,3S,5R,9R)-9-(tert-butyldimethylsiloxy)-3,5-dihydroxy-2,4,4,6-tetramethyltetradec-6-enoate | 245122-30-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl (6E,2S,3S,5R,9R)-9-(tert-butyldimethylsiloxy)-3,5-dihydroxy-2,4,4,6-tetramethyltetradec-6-enoate
• 英文别名: ethyl (E,2S,3S,5R,9R)-9-[tert-butyl(dimethyl)silyl]oxy-3,5-dihydroxy-2,4,4,6-tetramethyltetradec-6-enoate
• CAS: 245122-30-9
• 化学式: C₂₆H₅₂O₅Si
• 分子量: 472.781
• InChiKey: VMGSVHLGURORFR-JWMSFEQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.24
• 重原子数：
  32
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (6E,2S,3S,5R,9R)-9-(tert-butyldimethylsiloxy)-3,5-dihydroxy-2,4,4,6-tetramethyltetradec-6-enoate 在 camphor-10-sulfonic acid 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 2.0h， 生成 (6E,2S,3S,5R,9R)-9-(tert-butyldimethylsiloxy)-3,5-dihydroxy-3,5-O-isopropylidene-2,4,4,6-tetramethyltetradec-6-enal
  参考文献：
  名称：

  A Study Directed to the Asymmetric Synthesis of the Antineoplastic Macrolide Acutiphycin under Enantioselective Acyclic Stereoselection Based on Chiral Oxazaborolidinone-Promoted Asymmetic Aldol Reactions

  摘要：

  A shortening of the reaction path can be realized by using a series of the chiral oxazaborolidinone-promoted aldol reaction with respect to the practical synthesis of the (+)-acutiphycin seco acid derivative 5. The linear strategy is based on the utilization of five aldol reactions with a sequence of silyl nucleophiles, 7, 8, 35, 10, and 11, in the presence of stoichiometric amounts of the promoter, 1 or 2. The construction of the relative configuration between the stereogenic centers is diastereoselectively controlled by the stereochemistry of the promoter used in the enantioselective aldol reaction, which is nearly independent of that of the substrate (promoter control).

  DOI：

  10.1021/jo990342r
• 作为产物：
  描述：

  ethyl (-)-(3R)-3-hydroxyoctanoate 在 咪唑 、 2,6-二甲基吡啶 、 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 柠檬酸 、 (S)-4-Isopropyl-3-tosyl-[1,3,2]oxazaborolidin-5-one 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 34.58h， 生成 ethyl (6E,2S,3S,5R,9R)-9-(tert-butyldimethylsiloxy)-3,5-dihydroxy-2,4,4,6-tetramethyltetradec-6-enoate
  参考文献：
  名称：

  A Study Directed to the Asymmetric Synthesis of the Antineoplastic Macrolide Acutiphycin under Enantioselective Acyclic Stereoselection Based on Chiral Oxazaborolidinone-Promoted Asymmetic Aldol Reactions

  摘要：

  A shortening of the reaction path can be realized by using a series of the chiral oxazaborolidinone-promoted aldol reaction with respect to the practical synthesis of the (+)-acutiphycin seco acid derivative 5. The linear strategy is based on the utilization of five aldol reactions with a sequence of silyl nucleophiles, 7, 8, 35, 10, and 11, in the presence of stoichiometric amounts of the promoter, 1 or 2. The construction of the relative configuration between the stereogenic centers is diastereoselectively controlled by the stereochemistry of the promoter used in the enantioselective aldol reaction, which is nearly independent of that of the substrate (promoter control).

  DOI：

  10.1021/jo990342r