(+)-methyl (6S)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate | 197972-03-5

• 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 (6S)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate
• 英文别名: methyl (Z)-5-[(2S)-3,3-dimethyloxiran-2-yl]-3-(trimethylsilylmethyl)pent-2-enoate
• CAS: 197972-03-5
• 化学式: C₁₄H₂₆O₃Si
• 分子量: 270.444
• InChiKey: WBVWGRBMZTUSKM-MMRAYRKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-methyl (6S)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (1RS,3SR)-3-(hydroxymethyl)-2,2-dimethyl-4-methylenecyclohexanol
  参考文献：
  名称：

  Enantioselective synthesis of both enantiomers of γ-ionone, γ-damascone, karahana lactone and karahana ether

  摘要：

  A straightforward enantioselective synthesis of both enantiomers of the title compounds is described starting from enantiopure methyl (2S,6R)- or (2R,6S)-cis-2-hydroxy-gamma-cyclogeraniate. These versatile building blocks are obtained by biomimetic cyclization of methyl (6S)- or (6R)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate, respectively. The chiral information was encoded by a highly regioselective Sharpless asymmetric dihydroxylation of the corresponding diene. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00335-x
• 作为产物：
  描述：

  methyl Z-3-(diethylphosphoryloxy)-7-methyl-2,6-octadienoate 在 potassium osmate(VI) 、 甲基磺酰胺 bis(acetylacetonate)nickel(II) 、 (DHQD)2PHAL 、 potassium carbonate 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 32.0h， 生成 (+)-methyl (6S)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate
  参考文献：
  名称：

  Enantioselective synthesis of both enantiomers of γ-ionone, γ-damascone, karahana lactone and karahana ether

  摘要：

  A straightforward enantioselective synthesis of both enantiomers of the title compounds is described starting from enantiopure methyl (2S,6R)- or (2R,6S)-cis-2-hydroxy-gamma-cyclogeraniate. These versatile building blocks are obtained by biomimetic cyclization of methyl (6S)- or (6R)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate, respectively. The chiral information was encoded by a highly regioselective Sharpless asymmetric dihydroxylation of the corresponding diene. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00335-x

文献信息

• Use of a Lithiolactone in the Enantioselective Constructions of A/C seco-B and of A/B seco-C proTaxol Systems
  作者：Gilbert Stork、Takayuki Doi、Longbin Liu

  DOI：10.1016/s0040-4039(97)01793-0

  日期：1997.10

  We show that an unusual lithiolactone system is a useful starting point for the construction of various intermediates to the taxol structure. © 1997 Elsevier Science Ltd.

  我们表明，一个不寻常的硫代内酯体系是构建紫杉醇结构各种中间体的有用起点。©1997爱思唯尔科学有限公司。
• Synthesis of Two Key Fragments of the Complex Polyhalogenated Marine Meroterpenoid Azamerone
  作者：Simon D. Schnell、Anthony Linden、Karl Gademann

  DOI：10.1021/acs.orglett.9b00090

  日期：2019.2.15

  A concise route toward two advanced fragments in the context of the total synthesis of the unique natural product azamerone is reported. Key synthetic features include the enantioselective synthesis of an epoxysilane and its Lewis-acid-induced cyclization and the installation of the pyridazine ring via a formylation/condensation sequence. This route provides strategic insights into the chemistry of phthalazinediols, facilitating synthetic approaches toward this class of natural products.