methyl (5S)-5-[tert-butyl(dimethyl)silyl]oxy-6-oxohexanoate | 1224702-13-9

• 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: methyl (5S)-5-[tert-butyl(dimethyl)silyl]oxy-6-oxohexanoate
• CAS: 1224702-13-9
• 化学式: C₁₃H₂₆O₄Si
• 分子量: 274.433
• InChiKey: MKFBHGYDBLNNHG-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (5S)-5-[tert-butyl(dimethyl)silyl]oxy-6-oxohexanoate 在 4-甲基苯磺酸吡啶 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 (5S,6S)-methyl 5-(tert-butyldimethylsilyloxy)-6-((S)-2-methylpropan-2-ylsulfinylamino)hexanoate
  参考文献：
  名称：

  Diastereoconvergent Synthesis of trans-5-Hydroxy-6-Substituted-2-Piperidinones by Addition–Cyclization–Deprotection Process

  摘要：

  A diastereoselective one-pot approach to access trans-5-hydroxy-6-substituted-2-piperidinones by an addition-cyclization-deprotection process has been developed, in which the stereogenic center at the C-6 position was solely controlled by alpha-OTBS group. The utility of this transformation is demonstrated by the asymmetric synthesis of the enantiomer of (-)-CP-99,994.

  DOI：

  10.1021/ol5020812
• 作为产物：
  描述：

  在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 methyl (5S)-5-[tert-butyl(dimethyl)silyl]oxy-6-oxohexanoate
  参考文献：
  名称：

  Total synthesis of resolvin E2

  摘要：

  Resolvin E2 (2) was synthesized stereoselectively using the C1-8 and C15-20 aldehydes 6 and 9, which were connected to the C9-14 fragment by using Wittig reactions. The aldehyde 6 was prepared from the gamma-silyl alcohol (S)-20 by a sequence of reactions involving ozonolysis, oxidation with NalO(4), and the Wittig reaction of the resulting aldehyde with Ph3P=CHCHO, whereas the aldehyde 9 was synthesized from the corresponding gamma-silyl alcohol through epoxidation, reaction with Et2AlCN, and reduction with DIBAL-H. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.109

文献信息

• Diastereoconvergent Synthesis of <i>trans</i>-5-Hydroxy-6-Substituted-2-Piperidinones by Addition–Cyclization–Deprotection Process
  作者：Chang-Mei Si、Wei Huang、Zhen-Ting Du、Bang-Guo Wei、Guo-Qiang Lin

  DOI：10.1021/ol5020812

  日期：2014.8.15

  A diastereoselective one-pot approach to access trans-5-hydroxy-6-substituted-2-piperidinones by an addition-cyclization-deprotection process has been developed, in which the stereogenic center at the C-6 position was solely controlled by alpha-OTBS group. The utility of this transformation is demonstrated by the asymmetric synthesis of the enantiomer of (-)-CP-99,994.
• Total synthesis of resolvin E2
  作者：Yusuke Kosaki、Narihito Ogawa、Yuichi Kobayashi

  DOI：10.1016/j.tetlet.2010.01.109

  日期：2010.4

  Resolvin E2 (2) was synthesized stereoselectively using the C1-8 and C15-20 aldehydes 6 and 9, which were connected to the C9-14 fragment by using Wittig reactions. The aldehyde 6 was prepared from the gamma-silyl alcohol (S)-20 by a sequence of reactions involving ozonolysis, oxidation with NalO(4), and the Wittig reaction of the resulting aldehyde with Ph3P=CHCHO, whereas the aldehyde 9 was synthesized from the corresponding gamma-silyl alcohol through epoxidation, reaction with Et2AlCN, and reduction with DIBAL-H. (C) 2010 Elsevier Ltd. All rights reserved.