(1R)-1-{(4S,5S)-2-oxo-4-[(trityloxy)methyl]-1,3-oxazolidin-5-yl}pentadecyl mesylate | 1420382-91-7

• 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: (1R)-1-{(4S,5S)-2-oxo-4-[(trityloxy)methyl]-1,3-oxazolidin-5-yl}pentadecyl mesylate
• 英文别名: (4S,5S)-4-(trityloxymethyl)-5-[(R)1-(mesyloxy)pentadecyl]oxazolidin-2-one；[(1R)-1-[(4S,5S)-2-oxo-4-(trityloxymethyl)-1,3-oxazolidin-5-yl]pentadecyl] methanesulfonate
• CAS: 1420382-91-7
• 化学式: C₃₉H₅₃NO₆S
• 分子量: 663.919
• InChiKey: UHLKPQZJLQUYSG-QOEXFKEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  47
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  99.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R)-1-{(4S,5S)-2-oxo-4-[(trityloxy)methyl]-1,3-oxazolidin-5-yl}pentadecyl mesylate 在 三氟化硼乙醚 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 、 甲苯 为溶剂， 反应 24.0h， 生成 jaspine B
  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：

  (4S,5S)-5-((R)-1-hydroxypentadecyl)-4-(trityloxymethyl)oxazolidin-2-one 、 甲基磺酰氯 在 吡啶 作用下， 反应 12.0h， 以95%的产率得到(1R)-1-{(4S,5S)-2-oxo-4-[(trityloxy)methyl]-1,3-oxazolidin-5-yl}pentadecyl mesylate
  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

文献信息

• 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.