(4S,5S)-4-(hydroxymethyl)-5-[(R)1-(mesyloxy)pentadecyl]oxazolidin-2-one | 1340475-41-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5S)-4-(hydroxymethyl)-5-[(R)1-(mesyloxy)pentadecyl]oxazolidin-2-one
• 英文别名: (4S,5S)-4-hydroxymethyl-5-((R)-1-hydroxypentadecyl)oxazolidin-2-one；(4S,5S)-4-(hydroxymethyl)-5-[(1R)-1-hydroxypentadecyl]-1,3-oxazolidin-2-one
• CAS: 1340475-41-3
• 化学式: C₁₉H₃₇NO₄
• 分子量: 343.507
• InChiKey: XDOAVNZIOMPGLE-KSZLIROESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-(hydroxymethyl)-5-[(R)1-(mesyloxy)pentadecyl]oxazolidin-2-one 在 吡啶 、 4-二甲氨基吡啶 、 对甲苯磺酰氯 作用下， 反应 12.0h， 以94%的产率得到(3aS,6R,6aS)-6-tetradecyltetrahydrofuro[3,4-d]oxazol-2(3H)-one
  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：

  N-叔-丁基氧羰基-D-核-植物鞘氨醇 在 吡啶 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 48.5h， 生成 (4S,5S)-4-(hydroxymethyl)-5-[(R)1-(mesyloxy)pentadecyl]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

• An efficient synthesis and cytotoxic profile of D-ribo-phytosphingosine and its analogues
  作者：Milica Želinská、Kristína Vargová、Tatiana Pončáková、Martina Bago Pilátová、Miroslava Martinková、Monika Majirská、Juraj Kuchár、Miroslava Litecká、Lukáš Prchal

  DOI：10.1016/j.tet.2023.133541

  日期：2023.8

  l-erythrose chiron, which already contained the future C-3 and C-4 stereocentres of our target compounds. Construction of the remaining C-2 stereochemistry relied on aza-Claisen rearrangements to establish the desired vicinal aminoalcohol motif. The aliphatic chain was introduced by means of an olefin cross metathesis process. Completion of this phytosphingolipid synthesis was then achieved through the suitable

  在本文中，我们描述了从容易获得的l -赤藓糖 chiron开始有效合成d -核糖- 植物鞘氨醇及其类似物，其中已经包含了我们目标化合物的未来 C-3 和 C-4 立构中心。其余 C-2 立体化学的构建依赖于氮杂-克莱森重排来建立所需的邻位氨基醇基序。脂肪链是通过烯烃交叉复分解过程引入的。然后通过适当选择官能团相互转化并伴随选择性脱保护方案来完成该植物鞘脂合成。初步体外实验实验显示非天然的d-阿拉伯植物鞘氨醇3具有较高的抗增殖活性。HCl 与顺铂对评估的五种癌细胞系中的三种进行比较，IC 50值范围为 4.17 μM 至 7.63 μM。此外，化合物3。HCl对上述恶性细胞系的增殖具有比其天然立体化学同系物更好的抑制作用2。盐酸。
• 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.