(3R,4R,5S,7R,13R,14S,16S)-5-hydroxy-3,7-dimethyl-17-(oxan-2-yloxy)-4,13,14,16-tetrakis(phenylmethoxy)heptadec-9-yn-8-one | 251353-61-4

• 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: (3R,4R,5S,7R,13R,14S,16S)-5-hydroxy-3,7-dimethyl-17-(oxan-2-yloxy)-4,13,14,16-tetrakis(phenylmethoxy)heptadec-9-yn-8-one
• CAS: 251353-61-4
• 化学式: C₅₂H₆₆O₈
• 分子量: 819.091
• InChiKey: FNFGZWSIFIWRCZ-VEMAEQHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  60
• 可旋转键数：
  26
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R,4R,5S,7R,13R,14S,16S)-5-hydroxy-3,7-dimethyl-17-(oxan-2-yloxy)-4,13,14,16-tetrakis(phenylmethoxy)heptadec-9-yn-8-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 以85%的产率得到(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
  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：

  ((2R,3R)-3-Benzyloxy-2-methyl-3-(S)-oxiranyl-propoxy)-tert-butyl-diphenyl-silane 在 palladium on activated charcoal 正丁基锂 、 三氟甲磺酸 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 potassium carbonate 、 mercury dichloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 环己烷 、 乙酸乙酯 为溶剂， 生成 (3R,4R,5S,7R,13R,14S,16S)-5-hydroxy-3,7-dimethyl-17-(oxan-2-yloxy)-4,13,14,16-tetrakis(phenylmethoxy)heptadec-9-yn-8-one
  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.