3-O-[(3R,4R,5S,7S,13R,14S,16S)-17-azido-3,7-dimethyl-4,13,14,16-tetrakis(phenylmethoxy)heptadec-9-yn-5-yl] 1-O,2-O-bis(2-trimethylsilylethyl) (2R)-propane-1,2,3-tricarboxylate | 251353-66-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-O-[(3R,4R,5S,7S,13R,14S,16S)-17-azido-3,7-dimethyl-4,13,14,16-tetrakis(phenylmethoxy)heptadec-9-yn-5-yl] 1-O,2-O-bis(2-trimethylsilylethyl) (2R)-propane-1,2,3-tricarboxylate
• CAS: 251353-66-9
• 化学式: C₆₃H₈₉N₃O₁₀Si₂
• 分子量: 1104.58
• InChiKey: ZAFJUHWNINMWHL-MBGSTVLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.35
• 重原子数：
  78
• 可旋转键数：
  40
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-O-[(3R,4R,5S,7S,13R,14S,16S)-17-azido-3,7-dimethyl-4,13,14,16-tetrakis(phenylmethoxy)heptadec-9-yn-5-yl] 1-O,2-O-bis(2-trimethylsilylethyl) (2R)-propane-1,2,3-tricarboxylate 在 palladium on activated charcoal 盐酸 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 生成 AAL-toxin TA₁
  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 、 4-二甲氨基吡啶 、 palladium diacetate 、 lithium aluminium tetrahydride 、 三丁基膦 、 三(2-氯乙基)胺 、 4-甲基苯磺酸吡啶 、 乙酸酐 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 生成 3-O-[(3R,4R,5S,7S,13R,14S,16S)-17-azido-3,7-dimethyl-4,13,14,16-tetrakis(phenylmethoxy)heptadec-9-yn-5-yl] 1-O,2-O-bis(2-trimethylsilylethyl) (2R)-propane-1,2,3-tricarboxylate
  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.