(S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-2,3-dimethyl-5-thioxo-pyrrolidine-2-carbonitrile | 223663-85-2

• 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)-2,3-dimethyl-5-thioxo-pyrrolidine-2-carbonitrile
• 英文别名: (3S)-2,3-dimethyl-3-[(2S,3R,5R,6R)-6-methyl-3,5-bis(phenylmethoxy)oxan-2-yl]-5-sulfanylidenepyrrolidine-2-carbonitrile
• CAS: 223663-85-2
• 化学式: C₂₇H₃₂N₂O₃S
• 分子量: 464.629
• InChiKey: MUSPMHIGUALBSU-IIBGYZFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  5

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)-2,3-dimethyl-5-thioxo-pyrrolidine-2-carbonitrile 在 potassium tert-butylate 、 亚磷酸三乙酯 作用下， 以 xylene 、 叔丁醇 为溶剂， 生成 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：

  (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 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 (S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-2,3-dimethyl-5-thioxo-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

文献信息

• Total Synthesis of the Proposed Structure of (+)-Tolyporphin AO,O-Diacetate
  作者：Thomas G. Minehan、Yoshito Kishi

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

  日期：1999.4.1

  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.