(S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-(3-tert-butoxymethyl-3-methyl-5-oxo-4,5-dihydro-3H-pyrrol-2-yl)-meth-(Z)-ylidene]-2,3-dimethyl-pyrrolidine-2-carbonitrile | 223663-93-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-(3-tert-butoxymethyl-3-methyl-5-oxo-4,5-dihydro-3H-pyrrol-2-yl)-meth-(Z)-ylidene]-2,3-dimethyl-pyrrolidine-2-carbonitrile
• 英文别名: (3S,5Z)-2,3-dimethyl-3-[(2S,3R,5R,6R)-6-methyl-3,5-bis(phenylmethoxy)oxan-2-yl]-5-[[4-methyl-4-[(2-methylpropan-2-yl)oxymethyl]-2-oxo-3H-pyrrol-5-yl]methylidene]pyrrolidine-2-carbonitrile
• CAS: 223663-93-2
• 化学式: C₃₈H₄₉N₃O₅
• 分子量: 627.824
• InChiKey: ANTRVVCPQYBXHW-MXBOXUFXSA-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-(3-tert-butoxymethyl-3-methyl-5-oxo-4,5-dihydro-3H-pyrrol-2-yl)-meth-(Z)-ylidene]-2,3-dimethyl-pyrrolidine-2-carbonitrile 在 potassium tert-butylate 、 碘 、 potassium carbonate 作用下， 以 叔丁醇 、 二氯甲烷 为溶剂， 以80%的产率得到5-[(S)-4-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-iodo-meth-(Z)-ylidene]-4-methyl-pyrrolidin-(2Z)-ylidenemethyl]-4-tert-butoxymethyl-4-methyl-3,4-dihydro-pyrrol-2-one
  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：

  4-tert-Butoxymethyl-4-methyl-5-methylene-pyrrolidin-2-one 在 N-碘代丁二酰亚胺 、 potassium tert-butylate 、 亚磷酸三乙酯 作用下， 以 xylene 、 叔丁醇 、 苯 为溶剂， 生成 (S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-(3-tert-butoxymethyl-3-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