(2R,4S)-2,6-dimethyl-4-pentadecyl-1,3,6,2lambda5-dioxazaphosphocane 2-oxide | 185306-57-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (2R,4S)-2,6-dimethyl-4-pentadecyl-1,3,6,2lambda5-dioxazaphosphocane 2-oxide
• 英文别名: (2R,4S)-2,6-dimethyl-4-pentadecyl-1,3,6,2λ5-dioxazaphosphocane 2-oxide
• CAS: 185306-57-4
• 化学式: C₂₁H₄₄NO₃P
• 分子量: 389.559
• InChiKey: AETJFJAHBYUBIH-HFZDXXHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  26
• 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：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溴甲烷 、 (2R,4S)-2,6-dimethyl-4-pentadecyl-1,3,6,2lambda5-dioxazaphosphocane 2-oxide 以 乙醚 为溶剂， 反应 120.0h， 以63%的产率得到(2R,4S)-2,6,6-Trimethyl-2-oxo-4-pentadecyl-2λ⁵-[1,3,6,2]dioxazaphosphocan-6-ium; bromide
  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：

  (S)-1-pentadecyloxirane 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (2R,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

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).