(E,2S)-2-[(4-methoxyphenyl)methoxy]-2-methyl-8-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]oct-5-en-1-ol | 931113-80-3

• 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: (E,2S)-2-[(4-methoxyphenyl)methoxy]-2-methyl-8-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]oct-5-en-1-ol
• CAS: 931113-80-3
• 化学式: C₂₃H₃₆O₅
• 分子量: 392.536
• InChiKey: BQHYNYCNDJGQTN-BBKGRECJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E,2S)-2-[(4-methoxyphenyl)methoxy]-2-methyl-8-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]oct-5-en-1-ol 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 mercury(II) diacetate 、 4-甲基苯磺酸吡啶 、 双(三甲基硅烷基)氨基钾 、 戴斯-马丁氧化剂 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.83h， 生成 ((S,E)-3-(4-methoxybenzyloxy)-3-methyl-9-((S)-2-methyloxiran-2-yl)non-6-enyloxy)(tert-butyl)diphenylsilane
  参考文献：
  名称：

  Pectenotoxin-2 Synthetic Studies. 3. Assessment of the Capacity for Stereocontrolled Cyclization To Form the Entire C1−C26 Subunit Based upon the Double Bond Geometry Across C15-C16

  摘要：

  Second-generation synthetic routes to enantiopure sulfone 21 and aldehyde 24 are described. The union of these two intermediates by means of a Julia-Kocienski coupling gave rise to a series of E-configured building blocks that did not prove amenable to transannular cyclization. Alternatively, when the C15-C16 double bond was introduced with Z-geometry by Wittig olefination, spontaneous closure to generate a tetrahydrofuran culminated an ensuing direct dihydroxylation step. The structural assignment to 35, undergirded by detailed H-1 and C-13 NMR studies, is consistent with proper transannular bonding so as to deliver the entire C1-C26 fragment of PTX2.

  DOI：

  10.1021/jo062513f
• 作为产物：
  描述：

  tert-butyldimethyl((4-methylpent-4-en-1-yl)oxy)silane 在 potassium dioxotetrahydroxoosmate(VI) Hydroquinone 1,4-phthalazinediyl diether 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 potassium carbonate 、 间氯过氧苯甲酸 、 三苯基膦 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 95.5h， 生成 (E,2S)-2-[(4-methoxyphenyl)methoxy]-2-methyl-8-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]oct-5-en-1-ol
  参考文献：
  名称：

  Pectenotoxin-2 Synthetic Studies. 3. Assessment of the Capacity for Stereocontrolled Cyclization To Form the Entire C1−C26 Subunit Based upon the Double Bond Geometry Across C15-C16

  摘要：

  Second-generation synthetic routes to enantiopure sulfone 21 and aldehyde 24 are described. The union of these two intermediates by means of a Julia-Kocienski coupling gave rise to a series of E-configured building blocks that did not prove amenable to transannular cyclization. Alternatively, when the C15-C16 double bond was introduced with Z-geometry by Wittig olefination, spontaneous closure to generate a tetrahydrofuran culminated an ensuing direct dihydroxylation step. The structural assignment to 35, undergirded by detailed H-1 and C-13 NMR studies, is consistent with proper transannular bonding so as to deliver the entire C1-C26 fragment of PTX2.

  DOI：

  10.1021/jo062513f

文献信息

• Pectenotoxin-2 Synthetic Studies. 3. Assessment of the Capacity for Stereocontrolled Cyclization To Form the Entire C1−C26 Subunit Based upon the Double Bond Geometry Across C15-C16
  作者：Patrick D. O'Connor、Christopher K. Knight、Dirk Friedrich、Xiaowen Peng、Leo A. Paquette

  DOI：10.1021/jo062513f

  日期：2007.3.1

  Second-generation synthetic routes to enantiopure sulfone 21 and aldehyde 24 are described. The union of these two intermediates by means of a Julia-Kocienski coupling gave rise to a series of E-configured building blocks that did not prove amenable to transannular cyclization. Alternatively, when the C15-C16 double bond was introduced with Z-geometry by Wittig olefination, spontaneous closure to generate a tetrahydrofuran culminated an ensuing direct dihydroxylation step. The structural assignment to 35, undergirded by detailed H-1 and C-13 NMR studies, is consistent with proper transannular bonding so as to deliver the entire C1-C26 fragment of PTX2.