(2R,3R,4S,5R,6S)-3-[(2S)-2,3-bis(phenylmethoxy)propoxy]-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxane | 248263-68-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6S)-3-[(2S)-2,3-bis(phenylmethoxy)propoxy]-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxane
• CAS: 248263-68-5
• 化学式: C₅₀H₅₂O₇S
• 分子量: 797.025
• InChiKey: FCOFTJAPOGSOBX-HEAAWYMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  58
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-3-[(2S)-2,3-bis(phenylmethoxy)propoxy]-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxane 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 丙酮 为溶剂， 反应 0.05h， 生成 、
  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：

  (S)-4-[(benzyloxy)methyl]-2,2-dioxo-1,3,2-dioxathiolane 在 六甲基磷酰三胺 、 正丁基锂 、 2,2'-联喹啉 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 生成 (2R,3R,4S,5R,6S)-3-[(2S)-2,3-bis(phenylmethoxy)propoxy]-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxane
  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

• Total Synthesis of Calditol: Structural Clarification of this Typical Component of Archaea OrderSulfolobales
  作者：Yves Blériot、Edouard Untersteller、Benoît Fritz、Pierre Sinaÿ

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

  日期：2002.1.4

  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.