calditol | 164300-76-9

• 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: calditol
• 英文别名: (1S,2R,3R,4R,5S)-5-[(2S)-2,3-dihydroxypropoxy]-1-(hydroxymethyl)cyclopentane-1,2,3,4-tetrol
• CAS: 164300-76-9
• 化学式: C₉H₁₈O₈
• 分子量: 254.237
• InChiKey: JOKFCZVUUMLXSM-YQWDKWCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  151
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 calditol 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 4.0h， 生成 Acetic acid (1R,2R,3R,4R,5S)-2,3,4-triacetoxy-1-acetoxymethyl-5-((R)-2,3-diacetoxy-propoxy)-cyclopentyl ester
  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：

  (1S,2R,3S,4R,5S)-3,4-Bis-benzyloxy-1-benzyloxymethyl-5-((S)-2,3-bis-benzyloxy-propoxy)-cyclopentane-1,2-diol 在 10percent Pd/C 氢气 作用下， 以 甲醇 为溶剂， 反应 17.0h， 生成 calditol
  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

文献信息

• The Possibility of Involvement of “Cyclase” Enzyme of the Calditol Carbocycle with Broad Substrate Specificity in<i>Sulfolobus acidcaldarius</i>, a Typical Thermophilic Archaea
  作者：Noriaki Yamauchi、Norisuke Kamada、Hideyoshi Ueoka

  DOI：10.1246/cl.2006.1230

  日期：2006.11

  The cyclopentane ring of calditol, a characteristic lipid molecule of Sulfolobus, a major thermophilic Archaea, was biosynthesized from glucose directly, and galactose was converted to calditol with a similar extent to glucose. This finding indicates the possibility of the “cyclase” enzyme of the calditol carbocycle and the involvement of catalytic oxidoreduction at the C-4 of glucose with broad specificity.