(S)-2,2-Dimethyl-4-pentadecyl-[1,3]dioxolane | 185306-45-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2,2-Dimethyl-4-pentadecyl-[1,3]dioxolane
• 英文别名: (4S)-2,2-dimethyl-4-pentadecyl-1,3-dioxolane
• CAS: 185306-45-0
• 化学式: C₂₀H₄₀O₂
• 分子量: 312.536
• InChiKey: WYMDFORJVNBRAF-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2,2-Dimethyl-4-pentadecyl-[1,3]dioxolane 在 Amberlyst-A₁₅ 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 96.0h， 生成 (2S,4S)-2,6-dimethyl-4-pentadecyl-1,3,6,2lambda5-dioxazaphosphocane 2-oxide
  参考文献：
  名称：

  Synthesis of Optically Pure Cyclic Lipoidal Ammonium Salts and Evaluation of Inhibition of Protein Kinase C

  摘要：

  Stereoisomeric cyclic analogues of hexadecylphosphocholine (Miltefosine) and phosphatidylcholine, (2S,4S)-, (2R,4S)-, (2R,4R)-, and (2S,4R)-2,6,6-trimethyl-2-oxo-4-pentadecyl-1,3-dioxa-6-aza-2-phosphacyclooctane bromide (2a-d), and the enantiomers (S)- and (R)-N-(2-hydroxyethyl)-N-(2-hydroxyheptadecyl)-N,N-dimethylammonium iodide ((S)-and (R)-11) were prepared in good overall yields using optically pure glyceraldehyde surrogates as the starting materials. A four-step synthesis of the key intermediates ((S)- and (R)-1-pentadecyloxirane ((S)-and (R)-3) gave overall high optical purity and chemical yields. Approaches to the synthesis of these key intermediates utilizing asymmetric dihydroxylation on 1-pentadecene gave high chemical yields but only modest optical purity. All ammonium salts inhibited protein kinase C with the following values of IC50 (mu M): 2a (105), 2b (109), 2c (121), 2d (113).

  DOI：

  10.1021/jo961365y
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 72.0h， 以92%的产率得到(S)-2,2-Dimethyl-4-pentadecyl-[1,3]dioxolane
  参考文献：
  名称：

  Synthesis of Optically Pure Cyclic Lipoidal Ammonium Salts and Evaluation of Inhibition of Protein Kinase C

  摘要：

  Stereoisomeric cyclic analogues of hexadecylphosphocholine (Miltefosine) and phosphatidylcholine, (2S,4S)-, (2R,4S)-, (2R,4R)-, and (2S,4R)-2,6,6-trimethyl-2-oxo-4-pentadecyl-1,3-dioxa-6-aza-2-phosphacyclooctane bromide (2a-d), and the enantiomers (S)- and (R)-N-(2-hydroxyethyl)-N-(2-hydroxyheptadecyl)-N,N-dimethylammonium iodide ((S)-and (R)-11) were prepared in good overall yields using optically pure glyceraldehyde surrogates as the starting materials. A four-step synthesis of the key intermediates ((S)- and (R)-1-pentadecyloxirane ((S)-and (R)-3) gave overall high optical purity and chemical yields. Approaches to the synthesis of these key intermediates utilizing asymmetric dihydroxylation on 1-pentadecene gave high chemical yields but only modest optical purity. All ammonium salts inhibited protein kinase C with the following values of IC50 (mu M): 2a (105), 2b (109), 2c (121), 2d (113).

  DOI：

  10.1021/jo961365y

文献信息

• Synthesis of Optically Pure Cyclic Lipoidal Ammonium Salts and Evaluation of Inhibition of Protein Kinase C
  作者：M. Patricia Hubieki、Richard D. Gandour、Curtis L. Ashendel

  DOI：10.1021/jo961365y

  日期：1996.1.1

  Stereoisomeric cyclic analogues of hexadecylphosphocholine (Miltefosine) and phosphatidylcholine, (2S,4S)-, (2R,4S)-, (2R,4R)-, and (2S,4R)-2,6,6-trimethyl-2-oxo-4-pentadecyl-1,3-dioxa-6-aza-2-phosphacyclooctane bromide (2a-d), and the enantiomers (S)- and (R)-N-(2-hydroxyethyl)-N-(2-hydroxyheptadecyl)-N,N-dimethylammonium iodide ((S)-and (R)-11) were prepared in good overall yields using optically pure glyceraldehyde surrogates as the starting materials. A four-step synthesis of the key intermediates ((S)- and (R)-1-pentadecyloxirane ((S)-and (R)-3) gave overall high optical purity and chemical yields. Approaches to the synthesis of these key intermediates utilizing asymmetric dihydroxylation on 1-pentadecene gave high chemical yields but only modest optical purity. All ammonium salts inhibited protein kinase C with the following values of IC50 (mu M): 2a (105), 2b (109), 2c (121), 2d (113).