(4R)-2-(1'-bromooctadecyl)-4-(hydroxymethyl)-1,3-dioxolane | 143669-21-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: (4R)-2-(1'-bromooctadecyl)-4-(hydroxymethyl)-1,3-dioxolane
• 英文别名: [(4R)-2-(1-bromooctadecyl)-1,3-dioxolan-4-yl]methanol
• CAS: 143669-21-0；143669-22-1；143669-23-2；143669-24-3；143669-31-2；143669-32-3；143680-75-5；143705-56-0
• 化学式: C₂₂H₄₃BrO₃
• 分子量: 435.486
• InChiKey: UQDIXJOLBJXNBB-ITAUSPCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  26
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-2-(1'-bromooctadecyl)-4-(hydroxymethyl)-1,3-dioxolane 在 吡啶 、 lithium aluminium tetrahydride 、 三氯化铝 、 potassium tert-butylate 、 水 作用下， 以 乙醚 、 叔丁醇 为溶剂， 反应 5.0h， 生成 (2R,5R)-O-<<<(5-heptadecyl-1,4-dioxan-2-yl)methyl>-oxy>phospho>-β-bromoethanol
  参考文献：
  名称：

  Syntheses of all four stereoisomers which are conformationally constrained 1,4-dioxanyl analogs of the antineoplastic ether lipid ET-18-OCH3

  摘要：

  The syntheses of each of the four nearly optically pure stereoisomers of [[(5-heptadecyl-1,4-dioxan-2-yl)-methyl]oxy]phosphocholine (2,3,2',3') were performed by two parallel divergent sequences. Phosphocholines 2 and 3 were prepared via the corresponding 5-heptadecyl-2-(hydroxymethyl)-1,4-dioxanes 21 and 23, respectively, from the completely regiospecific mixed-hydride reductions of (1R,4S,5S)-4-heptadecyl-3,6,8-trioxabicyclo[3.2.1]octane (19) and (1R,4R,5S)-4-heptadecyl-3,6,8-trioxabicyclo[3.2.1]octane (20), respectively. The two 4-heptadecyl-3,6,8-trioxabicyclo[3.2.1]octanes 19 and 20 were the two separable products from an intramolecular cyclization reaction. By a parallel divergent sequence from the enantiomeric starting material, 3-O-benzyl-sn-glycerol (16'), the other two diastereomeric [[(5-heptadecyl-1,4-dioxan-2-yl)methyl]oxy]phosphocholines 2' and 3' were prepared. These four monocyclic [[(5-heptadecyl-1,4-dioxan-2-yl)methyl]oxy]phosphocholines (2,3,2',3') are conformationally constrained analogs of the antineoplastic and immunomodulatory ether lipid rac-2-O-methyl-1-O-octadecylglycero-3-phosphocholine (rac-1) (rac-ET-18-OCH3, rac-Edelfosine).

  DOI：

  10.1021/jo00049a021
• 作为产物：
  描述：

  2-bromo-1,1-dimethoxynonadecane 在 palladium dihydroxide 氢气 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 100.0 ℃ 、344.73 kPa 条件下， 反应 23.0h， 生成 (4R)-2-(1'-bromooctadecyl)-4-(hydroxymethyl)-1,3-dioxolane
  参考文献：
  名称：

  Syntheses of all four stereoisomers which are conformationally constrained 1,4-dioxanyl analogs of the antineoplastic ether lipid ET-18-OCH3

  摘要：

  The syntheses of each of the four nearly optically pure stereoisomers of [[(5-heptadecyl-1,4-dioxan-2-yl)-methyl]oxy]phosphocholine (2,3,2',3') were performed by two parallel divergent sequences. Phosphocholines 2 and 3 were prepared via the corresponding 5-heptadecyl-2-(hydroxymethyl)-1,4-dioxanes 21 and 23, respectively, from the completely regiospecific mixed-hydride reductions of (1R,4S,5S)-4-heptadecyl-3,6,8-trioxabicyclo[3.2.1]octane (19) and (1R,4R,5S)-4-heptadecyl-3,6,8-trioxabicyclo[3.2.1]octane (20), respectively. The two 4-heptadecyl-3,6,8-trioxabicyclo[3.2.1]octanes 19 and 20 were the two separable products from an intramolecular cyclization reaction. By a parallel divergent sequence from the enantiomeric starting material, 3-O-benzyl-sn-glycerol (16'), the other two diastereomeric [[(5-heptadecyl-1,4-dioxan-2-yl)methyl]oxy]phosphocholines 2' and 3' were prepared. These four monocyclic [[(5-heptadecyl-1,4-dioxan-2-yl)methyl]oxy]phosphocholines (2,3,2',3') are conformationally constrained analogs of the antineoplastic and immunomodulatory ether lipid rac-2-O-methyl-1-O-octadecylglycero-3-phosphocholine (rac-1) (rac-ET-18-OCH3, rac-Edelfosine).

  DOI：

  10.1021/jo00049a021

文献信息

• Syntheses of all four stereoisomers which are conformationally constrained 1,4-dioxanyl analogs of the antineoplastic ether lipid ET-18-OCH3
  作者：Richard I. Duclos、Alexandros Makriyannis

  DOI：10.1021/jo00049a021

  日期：1992.11

  The syntheses of each of the four nearly optically pure stereoisomers of [[(5-heptadecyl-1,4-dioxan-2-yl)-methyl]oxy]phosphocholine (2,3,2',3') were performed by two parallel divergent sequences. Phosphocholines 2 and 3 were prepared via the corresponding 5-heptadecyl-2-(hydroxymethyl)-1,4-dioxanes 21 and 23, respectively, from the completely regiospecific mixed-hydride reductions of (1R,4S,5S)-4-heptadecyl-3,6,8-trioxabicyclo[3.2.1]octane (19) and (1R,4R,5S)-4-heptadecyl-3,6,8-trioxabicyclo[3.2.1]octane (20), respectively. The two 4-heptadecyl-3,6,8-trioxabicyclo[3.2.1]octanes 19 and 20 were the two separable products from an intramolecular cyclization reaction. By a parallel divergent sequence from the enantiomeric starting material, 3-O-benzyl-sn-glycerol (16'), the other two diastereomeric [[(5-heptadecyl-1,4-dioxan-2-yl)methyl]oxy]phosphocholines 2' and 3' were prepared. These four monocyclic [[(5-heptadecyl-1,4-dioxan-2-yl)methyl]oxy]phosphocholines (2,3,2',3') are conformationally constrained analogs of the antineoplastic and immunomodulatory ether lipid rac-2-O-methyl-1-O-octadecylglycero-3-phosphocholine (rac-1) (rac-ET-18-OCH3, rac-Edelfosine).