(+/-)-9-<1,6-Di-O-benzyl-2a,5-didehydro-2a-carba-β-psicofuranosyl>adenine | 132150-31-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: (+/-)-9-<1,6-Di-O-benzyl-2a,5-didehydro-2a-carba-β-psicofuranosyl>adenine
• 英文别名: (1S,2R,5S)-5-(6-aminopurin-9-yl)-3,5-bis(phenylmethoxymethyl)cyclopent-3-ene-1,2-diol
• CAS: 132150-31-3
• 化学式: C₂₆H₂₇N₅O₄
• 分子量: 473.531
• InChiKey: VZCULULPYGUYBV-PLXFJCCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  128.54
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (+/-)-9-<1,6-Di-O-benzyl-2a,5-didehydro-2a-carba-β-psicofuranosyl>adenine 以59%的产率得到
  参考文献：
  名称：

  MARQUEZ, VICTOR E.;BODENTEICH, MICHAEL, NUCLEOSIDES AND NUCLEOTIDES, 10,(1991) N-3, C. 311-314

  摘要：

  DOI：
• 作为产物：
  描述：

  9-[(3aS,4S,6aR)-2-ethoxy-4,6-bis(phenylmethoxymethyl)-3a,6a-dihydrocyclopenta[d][1,3]dioxol-4-yl]purin-6-amine 以92%的产率得到
  参考文献：
  名称：

  MARQUEZ, VICTOR E.;BODENTEICH, MICHAEL, NUCLEOSIDES AND NUCLEOTIDES, 10,(1991) N-3, C. 311-314

  摘要：

  DOI：

文献信息

• Synthesis of (±)- psicoplanocin A.
  作者：Michael Bodenteich、Victor E Marquez

  DOI：10.1016/s0040-4039(00)98007-9

  日期：1990.1
• 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.
• BODENTEICH, MICHAEL;MARQUEZ, VICTOR E., TETRAHEDRON LETT., 31,(1990) N2, C. 5977-5980
  作者：BODENTEICH, MICHAEL、MARQUEZ, VICTOR E.

  DOI：——

  日期：——