(2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-3-((S)-2,3-bis-benzyloxy-propoxy)-2-hydroxy-cyclopentanone | 408512-59-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-3-((S)-2,3-bis-benzyloxy-propoxy)-2-hydroxy-cyclopentanone
• CAS: 408512-59-4
• 化学式: C₄₄H₄₆O₈
• 分子量: 702.844
• InChiKey: RPIFZLSXCUUHET-BARUUSNWSA-N

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-3-((S)-2,3-bis-benzyloxy-propoxy)-2-hydroxy-cyclopentanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以15 mg的产率得到(1R,2S,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：

  (1R,2R,3S,4R,5S)-3,4-Bis-benzyloxy-1-benzyloxymethyl-5-((S)-2,3-bis-benzyloxy-propoxy)-cyclopentane-1,2-diol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 potassium bromide 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 生成 (2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-3-((S)-2,3-bis-benzyloxy-propoxy)-2-hydroxy-cyclopentanone
  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