(4S,5S)-5-((R)-1-hydroxypentadecyl)-4-(trityloxymethyl)oxazolidin-2-one | 1340475-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (4S,5S)-5-((R)-1-hydroxypentadecyl)-4-(trityloxymethyl)oxazolidin-2-one
• 英文别名: (4S,5S)-5-[(1R)-1-hydroxypentadecyl]-4-(trityloxymethyl)-1,3-oxazolidin-2-one
• CAS: 1340475-40-2
• 化学式: C₃₈H₅₁NO₄
• 分子量: 585.827
• InChiKey: LXVJMVRJNJOXTC-PDHQKIGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  43
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5S)-5-((R)-1-hydroxypentadecyl)-4-(trityloxymethyl)oxazolidin-2-one 在 吡啶 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 对甲苯磺酰氯 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 、 甲苯 为溶剂， 反应 36.0h， 生成 (2R,3S,4S)-4-amino-2-tetradecyltetrahydrofuran-3-ol
  参考文献：
  名称：

  Stereochemically Reliable Syntheses of Pachastrissamine and Its 2-epi-Congener via Oxazolidinone Precursors from an Established Starting Material N-tert-Butoxycarbonyl-Protected Phytosphingosine

  摘要：

  Efficient, stereochemically unambiguous, total syntheses of pachastrissamine and its 2-epi-congener from the readily available common precursor (1R)-1-{(4S,5S)-2-oxo-4-[(trityl-oxy)methyl]-1,3-oxazolidin-5-yl}pentadecyl methanesulfonate are reported. Syntheses of (3aS,6R,6aR)- and (3aS,6S,6aR)-6-tetradecy-lhexahydro-2H-cyclopenta[d][1,3]oxazol-2-one by this route have unambiguously resolved a dispute over the structures of these products.

  DOI：

  10.1055/s-0032-1317506
• 作为产物：
  描述：

  tert-butyl ((2S,3S,4R)-3,4-dihydroxy-1-(trityloxy)octadecan-2-yl)carbamate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.5h， 以95%的产率得到(4S,5S)-5-((R)-1-hydroxypentadecyl)-4-(trityloxymethyl)oxazolidin-2-one
  参考文献：
  名称：

  Syntheses of sulfur and selenium analogues of pachastrissamine via double displacements of cyclic sulfate

  摘要：

  含有硫和硒原子的pachastrissamine生物等排素类化合物通过从一个环状硫酸盐中间体出发，经过二阴离子的顺序分子间和分子内SN2取代反应高效制备而成。这些类似物表现出与pachastrissamine相当的细胞毒性。

  DOI：

  10.1039/c1ob05920c

文献信息

• Syntheses of sulfur and selenium analogues of pachastrissamine via double displacements of cyclic sulfate
  作者：Hongjun Jeon、Hoon Bae、Dong Jae Baek、Young-Shin Kwak、Deukjoon Kim、Sanghee Kim

  DOI：10.1039/c1ob05920c

  日期：——

  Bioisosteric analogues of pachastrissamine that contain sulfur and selenium atoms replacing the oxygen in the ring system, were efficiently prepared from a cyclic sulfate intermediate by sequential intermolecular and intramolecular SN2 displacement reactions of the dianions. The analogues exhibited cytotoxicities comparable to that of pachastrissamine.

  含有硫和硒原子的pachastrissamine生物等排素类化合物通过从一个环状硫酸盐中间体出发，经过二阴离子的顺序分子间和分子内SN2取代反应高效制备而成。这些类似物表现出与pachastrissamine相当的细胞毒性。
• Stereochemically Reliable Syntheses of Pachastrissamine and Its 2-epi-Congener via Oxazolidinone Precursors from an Established Starting Material N-tert-Butoxycarbonyl-Protected Phytosphingosine
  作者：Dongjoo Lee、Sanghee Kim、Hoon Bae、Hongjun Jeon、Dong Baek

  DOI：10.1055/s-0032-1317506

  日期：——

  Efficient, stereochemically unambiguous, total syntheses of pachastrissamine and its 2-epi-congener from the readily available common precursor (1R)-1-(4S,5S)-2-oxo-4-[(trityl-oxy)methyl]-1,3-oxazolidin-5-yl}pentadecyl methanesulfonate are reported. Syntheses of (3aS,6R,6aR)- and (3aS,6S,6aR)-6-tetradecy-lhexahydro-2H-cyclopenta[d][1,3]oxazol-2-one by this route have unambiguously resolved a dispute over the structures of these products.