(2R,3R,4S)-2,3,6-Tris-benzyloxy-4-((S)-2,3-bis-benzyloxy-propoxy)-5-oxo-hexanal | 248263-71-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (2R,3R,4S)-2,3,6-Tris-benzyloxy-4-((S)-2,3-bis-benzyloxy-propoxy)-5-oxo-hexanal
• 英文别名: (2R,3R,4S)-4-[(2S)-2,3-bis(phenylmethoxy)propoxy]-5-oxo-2,3,6-tris(phenylmethoxy)hexanal
• CAS: 248263-71-0
• 化学式: C₄₄H₄₆O₈
• 分子量: 702.844
• InChiKey: INNUHPSSTBCBMC-JEBCDFCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  52
• 可旋转键数：
  24
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-2,3,6-Tris-benzyloxy-4-((S)-2,3-bis-benzyloxy-propoxy)-5-oxo-hexanal 在 samarium diiodide 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以2.9 g的产率得到(3S,4R,5S)-3,4-Bis-benzyloxy-1-benzyloxymethyl-5-((S)-2,3-bis-benzyloxy-propoxy)-cyclopentane-1,2-diol
  参考文献：
  名称：

  Total Synthesis of Calditol: Structural Clarification of this Typical Component of Archaea OrderSulfolobales

  摘要：

  The original structure of calditol-that is, an open-chain branched nonitol-has recently been questioned by various research groups and cyclopentane-based structures have been proposed. To unambiguously clear up this confusion, four isomeric cyclopentane candidates 26-29 have been synthesized. Of these, compound 27 was found to be fully identical to the natural product present in Sulfolobus solfataricus (A.T.C.C. 49155). The synthesis of 27 uses a samarium-diiodide-induced pinacolization reaction of the ketoaldehyde 15 as the critical step.

  DOI：

  10.1002/1521-3765(20020104)8:1<240::aid-chem240>3.0.co;2-g
• 作为产物：
  描述：

  (2S,3R,4R,5R)-2,3,6-Tris-benzyloxy-4-((S)-2,3-bis-benzyloxy-propoxy)-hexane-1,5-diol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.08h， 生成 (2R,3R,4S)-2,3,6-Tris-benzyloxy-4-((S)-2,3-bis-benzyloxy-propoxy)-5-oxo-hexanal
  参考文献：
  名称：

  Total Synthesis of Calditol: Structural Clarification of this Typical Component of Archaea OrderSulfolobales

  摘要：

  The original structure of calditol-that is, an open-chain branched nonitol-has recently been questioned by various research groups and cyclopentane-based structures have been proposed. To unambiguously clear up this confusion, four isomeric cyclopentane candidates 26-29 have been synthesized. Of these, compound 27 was found to be fully identical to the natural product present in Sulfolobus solfataricus (A.T.C.C. 49155). The synthesis of 27 uses a samarium-diiodide-induced pinacolization reaction of the ketoaldehyde 15 as the critical step.

  DOI：

  10.1002/1521-3765(20020104)8:1<240::aid-chem240>3.0.co;2-g