(2S)-1-[(2R,3R,4S,5R,6S)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-3-phenylmethoxypropan-2-ol | 248263-67-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-1-[(2R,3R,4S,5R,6S)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-3-phenylmethoxypropan-2-ol
• CAS: 248263-67-4
• 化学式: C₄₃H₄₆O₇S
• 分子量: 706.9
• InChiKey: AOQMMKFZQXSDJA-KRLRLXNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  51
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S)-1-[(2R,3R,4S,5R,6S)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-3-phenylmethoxypropan-2-ol 在 N-溴代丁二酰亚胺(NBS) 、 水 、 sodium hydride 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 3.05h， 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：

  (R)-(+)-3-苄氧基-1,2-丙二醇 在 六甲基磷酰三胺 、 ruthenium trichloride 、 sodium periodate 、 正丁基锂 、 氯化亚砜 、 2,2'-联喹啉 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 4.75h， 生成 (2S)-1-[(2R,3R,4S,5R,6S)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-3-phenylmethoxypropan-2-ol
  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