(2S,2'R,5'S,2''R,5''R,2'''S,5'''R,2''''S)-2,5',2''',2''''-Tetramethyl-icosahydro-[2,2';5',2'';5'',2''';5''',2'''']quinquefuran-5,5''''-diol | 371783-99-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2S,2'R,5'S,2''R,5''R,2'''S,5'''R,2''''S)-2,5',2''',2''''-Tetramethyl-icosahydro-[2,2';5',2'';5'',2''';5''',2'''']quinquefuran-5,5''''-diol
• 英文别名: (5S)-5-[(2R,5S)-5-[(2R,5R)-5-[(2S,5R)-5-[(2S)-5-hydroxy-2-methyloxolan-2-yl]-2-methyloxolan-2-yl]oxolan-2-yl]-5-methyloxolan-2-yl]-5-methyloxolan-2-ol
• CAS: 371783-99-2
• 化学式: C₂₄H₄₀O₇
• 分子量: 440.577
• InChiKey: OPOOJEREHSVSSP-BMNAQMGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,2'R,5'S,2''R,5''R,2'''S,5'''R,2''''S)-2,5',2''',2''''-Tetramethyl-icosahydro-[2,2';5',2'';5'',2''';5''',2'''']quinquefuran-5,5''''-diol 在 氧气 、 rose bengal 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.0h， 生成 (E)-(S)-6-Hydroperoxy-2-[(2S,5R,2'R,5'R,2''S,5''R)-5''-((E)-(S)-5-hydroperoxy-1-hydroxy-1,5-dimethyl-hex-3-enyl)-2,2''-dimethyl-dodecahydro-[2,2';5',2'']terfuran-5-yl]-6-methyl-hept-4-en-2-ol
  参考文献：
  名称：

  Total synthesis and determination of the absolute configuration of (−)-longilene peroxide

  摘要：

  The first asymmetric total synthesis of (-)-longilene peroxide (1) has been achieved starting from the optically active C-2-symmetric diepoxide 5 through the concept of two-directional synthesis utilizing its intrinsic molecular symmetry. Thus, the unknown absolute configuration of longilene peroxide has been determined by this synthesis as shown in the structural formula 1. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01239-4
• 作为产物：
  描述：

  (3S,6S)-6-[(2S,5R,2'R,5'R,2''S,5''R)-2,2''-Dimethyl-5''-((1S,4S)-1,4,5-trihydroxy-1,5-dimethyl-hexyl)-dodecahydro-[2,2';5',2'']terfuran-5-yl]-2-methyl-heptane-2,3,6-triol 在 sodium periodate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.25h， 以99%的产率得到(2S,2'R,5'S,2''R,5''R,2'''S,5'''R,2''''S)-2,5',2''',2''''-Tetramethyl-icosahydro-[2,2';5',2'';5'',2''';5''',2'''']quinquefuran-5,5''''-diol
  参考文献：
  名称：

  Total synthesis and determination of the absolute configuration of (−)-longilene peroxide

  摘要：

  The first asymmetric total synthesis of (-)-longilene peroxide (1) has been achieved starting from the optically active C-2-symmetric diepoxide 5 through the concept of two-directional synthesis utilizing its intrinsic molecular symmetry. Thus, the unknown absolute configuration of longilene peroxide has been determined by this synthesis as shown in the structural formula 1. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01239-4

文献信息

• Total synthesis and determination of the absolute configuration of (−)-longilene peroxide
  作者：Yoshiki Morimoto、Toshiyuki Iwai、Takamasa Kinoshita

  DOI：10.1016/s0040-4039(01)01239-4

  日期：2001.9

  The first asymmetric total synthesis of (-)-longilene peroxide (1) has been achieved starting from the optically active C-2-symmetric diepoxide 5 through the concept of two-directional synthesis utilizing its intrinsic molecular symmetry. Thus, the unknown absolute configuration of longilene peroxide has been determined by this synthesis as shown in the structural formula 1. (C) 2001 Elsevier Science Ltd. All rights reserved.