(2S,4S,5R,11S,13S,14R,15R)-11,15-dimethyl-2,4,5,14-tetrakis(phenylmethoxy)heptadec-8-yne-1,13-diol | 251353-64-7

• 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: (2S,4S,5R,11S,13S,14R,15R)-11,15-dimethyl-2,4,5,14-tetrakis(phenylmethoxy)heptadec-8-yne-1,13-diol
• CAS: 251353-64-7
• 化学式: C₄₇H₆₀O₆
• 分子量: 720.99
• InChiKey: VMMWTFDQIGPTAN-MVAUIFNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  53
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R,11S,13S,14R,15R)-11,15-dimethyl-2,4,5,14-tetrakis(phenylmethoxy)heptadec-8-yne-1,13-diol 在 4-二甲氨基吡啶 、 三(2-氯乙基)胺 、 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (R)-3-Carboxy-pentanedioic acid mono-[(1S,3S,9R,10S,12S)-13-azido-9,10,12-tris-benzyloxy-1-((1R,2R)-1-benzyloxy-2-methyl-butyl)-3-methyl-tridec-5-ynyl] ester
  参考文献：
  名称：

  Total synthesis of AAL-toxin TA1

  摘要：

  Two alternative synthetic routes of the left-half segment 5 have been developed. Efficient condensation between the left and right segments followed by Pd-catalyzed deoxygenation and further elaboration achieved the first total synthesis of AAL-toxin TA(1). This allowed us to synthesize various AAL-toxin analogs which would be useful for investigating SAR studies of AAL-toxins. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01322-2
• 作为产物：
  描述：

  (3R,4R,5S,7R,13R,14S,16S)-4,13,14,16-Tetrakis-benzyloxy-3,7-dimethyl-17-(tetrahydro-pyran-2-yloxy)-heptadec-9-yne-5,8-diol 在 吡啶 、 palladium diacetate 、 lithium aluminium tetrahydride 、 三丁基膦 、 4-甲基苯磺酸吡啶 、 乙酸酐 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (2S,4S,5R,11S,13S,14R,15R)-11,15-dimethyl-2,4,5,14-tetrakis(phenylmethoxy)heptadec-8-yne-1,13-diol
  参考文献：
  名称：

  Total synthesis of AAL-toxin TA1

  摘要：

  Two alternative synthetic routes of the left-half segment 5 have been developed. Efficient condensation between the left and right segments followed by Pd-catalyzed deoxygenation and further elaboration achieved the first total synthesis of AAL-toxin TA(1). This allowed us to synthesize various AAL-toxin analogs which would be useful for investigating SAR studies of AAL-toxins. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01322-2

文献信息

• Total synthesis of AAL-toxin TA1
  作者：Hideaki Oikawa、Daisuke Yamawaki、Takashi Kagawa、Akitami Ichihara

  DOI：10.1016/s0040-4039(99)01322-2

  日期：1999.9

  Two alternative synthetic routes of the left-half segment 5 have been developed. Efficient condensation between the left and right segments followed by Pd-catalyzed deoxygenation and further elaboration achieved the first total synthesis of AAL-toxin TA(1). This allowed us to synthesize various AAL-toxin analogs which would be useful for investigating SAR studies of AAL-toxins. (C) 1999 Elsevier Science Ltd. All rights reserved.