(3aS,4S,5R,6R,6aR)-5,6-Bis-benzyloxy-3a-benzyloxymethyl-4-((S)-2,3-bis-benzyloxy-propoxy)-tetrahydro-cyclopenta[1,3]dioxol-2-one | 248263-74-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4S,5R,6R,6aR)-5,6-Bis-benzyloxy-3a-benzyloxymethyl-4-((S)-2,3-bis-benzyloxy-propoxy)-tetrahydro-cyclopenta[1,3]dioxol-2-one
• CAS: 248263-74-3
• 化学式: C₄₅H₄₆O₉
• 分子量: 730.855
• InChiKey: AQSUVBITASXKFK-UMJBVAFVSA-N

反应信息

• 作为反应物：
  描述：

  (3aS,4S,5R,6R,6aR)-5,6-Bis-benzyloxy-3a-benzyloxymethyl-4-((S)-2,3-bis-benzyloxy-propoxy)-tetrahydro-cyclopenta[1,3]dioxol-2-one 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以98%的产率得到(1R,2R,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：

  (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 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (3aS,4S,5R,6R,6aR)-5,6-Bis-benzyloxy-3a-benzyloxymethyl-4-((S)-2,3-bis-benzyloxy-propoxy)-tetrahydro-cyclopenta[1,3]dioxol-2-one
  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