(1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enylphenoxythiocarboxylate | 133119-18-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enylphenoxythiocarboxylate
• 英文别名: [(1S,2S,5S)-2-(2,6-diaminopurin-9-yl)-5-(phenylmethoxymethyl)cyclopent-3-en-1-yl]oxy-phenoxymethanethione
• CAS: 133119-18-3
• 化学式: C₂₅H₂₄N₆O₃S
• 分子量: 488.57
• InChiKey: CLAMQKYVWVJGLK-CUWPLCDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  155
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enylphenoxythiocarboxylate 在 吡啶 、 甲醇 、 偶氮二异丁腈 、 三氟化硼乙醚 、 氨 、 三正丁基氢锡 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 5.17h， 生成 (-)-卡巴韦
  参考文献：
  名称：

  Total synthesis of (–)-carbovir

  摘要：

  Optically pure (-)-carbovir has been prepared by two different routes involving stereospecific opening of chiral cyclopentene epoxides by substituted purines. Introduction of the 2',3' unsaturation was accomplished by mesylate elimination, either after introduction of the purine (Route 1), or earlier in the sequence, producing a novel vinyl epoxide (Route 2).

  DOI：

  10.1039/p19910002479
• 作为产物：
  描述：

  (1S,2S,5R)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hex-3-ene 在 4-二甲氨基吡啶 、 15-冠醚-5 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 5.08h， 生成 (1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enylphenoxythiocarboxylate
  参考文献：
  名称：

  Total synthesis of (–)-carbovir

  摘要：

  Optically pure (-)-carbovir has been prepared by two different routes involving stereospecific opening of chiral cyclopentene epoxides by substituted purines. Introduction of the 2',3' unsaturation was accomplished by mesylate elimination, either after introduction of the purine (Route 1), or earlier in the sequence, producing a novel vinyl epoxide (Route 2).

  DOI：

  10.1039/p19910002479

文献信息

• Total synthesis of (–)-carbovir
  作者：Martin F. Jones、Peter L. Myers、Colin A. Robertson、Richard Storer、Christopher Williamson

  DOI：10.1039/p19910002479

  日期：——

  Optically pure (-)-carbovir has been prepared by two different routes involving stereospecific opening of chiral cyclopentene epoxides by substituted purines. Introduction of the 2',3' unsaturation was accomplished by mesylate elimination, either after introduction of the purine (Route 1), or earlier in the sequence, producing a novel vinyl epoxide (Route 2).