(+/-)-9-<1,6-Di-O-benzyl-3,4-O-(ethoxymethylene)-2a,5-didehydro-2a-carba-β-psicofuranosyl>adenine | 132150-11-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (+/-)-9-<1,6-Di-O-benzyl-3,4-O-(ethoxymethylene)-2a,5-didehydro-2a-carba-β-psicofuranosyl>adenine
• CAS: 132150-11-9；132202-96-1；151215-07-5
• 化学式: C₂₉H₃₁N₅O₅
• 分子量: 529.596
• InChiKey: IEMNKFLRTBXTKQ-RDVRGBNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  115.77
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (+/-)-9-<1,6-Di-O-benzyl-3,4-O-(ethoxymethylene)-2a,5-didehydro-2a-carba-β-psicofuranosyl>adenine 在 盐酸 、 ammonium hydroxide 、 氨 、 sodium 作用下， 反应 18.0h， 生成 (+/-)-Psicoplanocin A
  参考文献：
  名称：

  Synthesis of (±)- psicoplanocin A.

  摘要：

  DOI：

  10.1016/s0040-4039(00)98007-9
• 作为产物：
  描述：

  (+/-)-2-N-(5-Amino-6-chloropyrimidin-4-yl)-1,6-di-O-benzyl-2a,5-didehydro-2a-carba-β-psicofuranosylamine 在 盐酸 、 氨 作用下， 以 甲醇 为溶剂， 反应 36.0h， 生成 (+/-)-9-<1,6-Di-O-benzyl-3,4-O-(ethoxymethylene)-2a,5-didehydro-2a-carba-β-psicofuranosyl>adenine
  参考文献：
  名称：

  Synthesis of (±)- psicoplanocin A.

  摘要：

  DOI：

  10.1016/s0040-4039(00)98007-9

文献信息

• Synthesis of carbocyclic analogs of 1-.beta.-D-psicofuranosyl nucleosides. psico-Cyclopentenyladenosine (psicoplanocin A) and psico-cyclopentenylcytosine
  作者：Michael Bodenteich、Victor E. Marquez、Joseph J. Barchi、Wendy H. Hallows、Barry M. Goldstein、John S. Driscoll

  DOI：10.1021/jo00074a030

  日期：1993.10

  Psicoplanocin A (4a) and psico-cyclopentenylcytosine (4b) represent the first two known examples of carbocyclic ketohexose nucleosides. These two stable compounds combine structural features of two known classes of natural products: neplanocin A and the ketohexose nucleosides psicofuranine (1a) and decoynine (2). Both compounds were synthesized in racemic form from (+/-)-cyclopentenone 5, which in turn was available froM D-ribonolactone. Construction of the surrogate glycon moiety commenced with the attachment of a protected hydroxymethyl fragment onto the ketone carbonyl of 5 via nucleophilic addition of [(benzoyloxy)methyl]lithium to give intermediate 7. Introduction of the requisite nitrogen at the tertiary allylic carbon of 7 was achieved by the BF3.OEt2-catalyzed addition of hydrazoic acid to a generated transitional allylic cation. This method produced the epimeric azides 8a and 8b, and following conversion of the beta-azide (8a) to the corresponding carbocyclic amine, the purine and pyrimidine rings of psicoplanocin A and psico-cyclopentenylcytosine were constructed by conventional methods. An X-ray crystallographic analysis corroborated the structure of psicoplanocin A determined from NOE experiments on the epimeric azides. Both psicoplanocin A and psico-cyclopentenylcytosine were found to be devoid of cell cytotoxicity and in vitro antiviral activity.