(S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-(4-tert-butoxymethyl-4-methyl-5-oxo-4,5-dihydro-3H-pyrrol-2-yl)-meth-(Z)-ylidene]-2,3-dimethyl-pyrrolidine-2-carbonitrile | 223663-97-6

• 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: (S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-(4-tert-butoxymethyl-4-methyl-5-oxo-4,5-dihydro-3H-pyrrol-2-yl)-meth-(Z)-ylidene]-2,3-dimethyl-pyrrolidine-2-carbonitrile
• CAS: 223663-97-6
• 化学式: C₃₈H₄₉N₃O₅
• 分子量: 627.824
• InChiKey: NPWPEJHEGHKRAT-QBZNBRBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  46.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  102.17
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-(4-tert-butoxymethyl-4-methyl-5-oxo-4,5-dihydro-3H-pyrrol-2-yl)-meth-(Z)-ylidene]-2,3-dimethyl-pyrrolidine-2-carbonitrile 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以89%的产率得到(S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-(4-tert-butoxymethyl-4-methyl-5-thioxo-4,5-dihydro-3H-pyrrol-2-yl)-meth-(Z)-ylidene]-2,3-dimethyl-pyrrolidine-2-carbonitrile
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure of (+)-Tolyporphin AO,O-Diacetate

  摘要：

  Four monocyclic precursors were assembled in the total synthesis of the proposed structure 1-A of (+)-tolyporphin A O,O-diacetate (X=Ac). Comparison of the spectroscopic data demonstrated that synthetic tolyporphin O,O-diacetate did not match the O,O-diacetate prepared from natural (+)-tolyporphin A (X=H), calling for a structural revision of this class of natural products. On the basis of a series of NMR experiments including synthetic intermediates, the structure of tolyporphin A is concluded to be 1-B, in which the configurations of quaternary centers C7 and C17 are opposite to those in the originally proposed structure.

  DOI：

  10.1002/(sici)1521-3773(19990401)38:7<923::aid-anie923>3.0.co;2-7
• 作为产物：
  描述：

  (S)-4-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-4-methyl-5-methylene-pyrrolidin-2-one 在 劳森试剂 、 亚磷酸三乙酯 作用下， 以 甲醇 、 甲苯 、 xylene 为溶剂， 生成 (S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-(4-tert-butoxymethyl-4-methyl-5-oxo-4,5-dihydro-3H-pyrrol-2-yl)-meth-(Z)-ylidene]-2,3-dimethyl-pyrrolidine-2-carbonitrile
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure of (+)-Tolyporphin AO,O-Diacetate

  摘要：

  Four monocyclic precursors were assembled in the total synthesis of the proposed structure 1-A of (+)-tolyporphin A O,O-diacetate (X=Ac). Comparison of the spectroscopic data demonstrated that synthetic tolyporphin O,O-diacetate did not match the O,O-diacetate prepared from natural (+)-tolyporphin A (X=H), calling for a structural revision of this class of natural products. On the basis of a series of NMR experiments including synthetic intermediates, the structure of tolyporphin A is concluded to be 1-B, in which the configurations of quaternary centers C7 and C17 are opposite to those in the originally proposed structure.

  DOI：

  10.1002/(sici)1521-3773(19990401)38:7<923::aid-anie923>3.0.co;2-7