methyl (1S,2R,3S,4R,5S,6R)-2,3-dihydroxy-6-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>bicyclo<2.2.1>hept-5-ylcarboxylate | 156325-12-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl (1S,2R,3S,4R,5S,6R)-2,3-dihydroxy-6-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>bicyclo<2.2.1>hept-5-ylcarboxylate
• 英文别名: methyl (1S,2S,3R,4R,5R,6S)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5,6-dihydroxybicyclo[2.2.1]heptane-2-carboxylate
• CAS: 156325-12-1
• 化学式: C₁₄H₂₂O₆
• 分子量: 286.325
• InChiKey: SWOGHWROJJEMFB-QSDIAOLASA-N

物化性质

• 沸点：
  384.7±42.0 °C(predicted)
• 密度：
  1.303±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R,3S,4R,5S,6R)-2,3-dihydroxy-6-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>bicyclo<2.2.1>hept-5-ylcarboxylate 在 盐酸 、 sodium periodate 、 双氧水 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 51.33h， 生成 methyl (1S,2R,6S,7R)-4,4-dimethyl-9-formyl-3,5-dioxatricyclo<5.2.1.0^2,6>dec-8-en-8-ylcarboxylate
  参考文献：
  名称：

  Stereocontrolled synthetic entries to homochiral hydroxylated norbornene derivatives. Formal synthesis of some carbocyclic nucleosides.

  摘要：

  Several homochiral hydroxylated norbornene derivatives have been synthesized from D-mannitol. Stereocontrolled Diels-Alder cycloadditions and stereospecific hydroxylations are key processes for the creation of the stereogenic centers in the target molecules. These compounds are real or potential precursors in the synthesis of carbocyclic nucleosides and related products.

  DOI：

  10.1016/s0957-4166(00)80493-0
• 作为产物：
  描述：

  methyl (1R,2S,3R,4S)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>bicyclo(2.2.1)-5-hepten-2-ylcarboxylate 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 24.0h， 以81%的产率得到methyl (1S,2R,3S,4R,5S,6R)-2,3-dihydroxy-6-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>bicyclo<2.2.1>hept-5-ylcarboxylate
  参考文献：
  名称：

  Stereocontrolled synthetic entries to homochiral hydroxylated norbornene derivatives. Formal synthesis of some carbocyclic nucleosides.

  摘要：

  Several homochiral hydroxylated norbornene derivatives have been synthesized from D-mannitol. Stereocontrolled Diels-Alder cycloadditions and stereospecific hydroxylations are key processes for the creation of the stereogenic centers in the target molecules. These compounds are real or potential precursors in the synthesis of carbocyclic nucleosides and related products.

  DOI：

  10.1016/s0957-4166(00)80493-0