(1β,2α,5α)-1-N-(5-amino-6-chloropyrimidin-4-yl)-2,5-bis(benzyloxy)-3-<(benzyloxy)methyl>-3-cyclopentenylamine | 139607-44-6

• 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: (1β,2α,5α)-1-N-(5-amino-6-chloropyrimidin-4-yl)-2,5-bis(benzyloxy)-3-<(benzyloxy)methyl>-3-cyclopentenylamine
• CAS: 139607-44-6
• 化学式: C₃₁H₃₁ClN₄O₃
• 分子量: 543.065
• InChiKey: CGNIHJDPXAQZFI-WIIGKZCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  91.52
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1β,2α,5α)-1-N-(5-amino-6-chloropyrimidin-4-yl)-2,5-bis(benzyloxy)-3-<(benzyloxy)methyl>-3-cyclopentenylamine 在 盐酸 、 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 9-<(1β,2α,5α)-2,5-dihydroxy-3-(hydroxymethyl)-3-cyclopenten-1-yl>-6-chloropurine
  参考文献：
  名称：

  Synthesis and structural determination of (.+-.)-neplanocin F

  摘要：

  Neplanocin F (2), a minor constituent of the family of neplanocin antibiotics, was synthesized as a racemate in 12 steps from cyclopentenone 3/4, which in turn was available from D-ribonolactone. The carbocyclic ring of neplanocin F corresponds to the allylic rearranged isomer of the biologically active agent neplanocin A. Regiospecific reduction of the racemic cyclopentenone 3/4 and protection of the resulting alpha-alcohol as a benzyl ether 6 produced, after removal of the isopropylidene moiety, a compound (7) having allylic and homoallylic secondary alcohol functionalities. Differences in the reactivity of these two secondary alcohols were successfully manipulated to prepare the homoallylic substituted azide 14, which was then reduced and converted to the desired adenine ring by conventional methods. The spectral properties of the synthesized material [(+/-)-neplanocin F] were identical to those of the natural product, except for its lack of optical rotation. X-ray crystallographic analysis helped corroborate the structure. In contrast to its bioactive isomer, neoplanocin A, neplanocin F was devoid of cytotoxicity and in vitro antiviral activity.

  DOI：

  10.1021/jo00033a031
• 作为产物：
  描述：

  (1α,4α,5β)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4-hydroxy-5-azido-2-cyclopentene 在 Lindlar's catalyst 氢气 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 正丁醇 为溶剂， 反应 49.0h， 生成 (1β,2α,5α)-1-N-(5-amino-6-chloropyrimidin-4-yl)-2,5-bis(benzyloxy)-3-<(benzyloxy)methyl>-3-cyclopentenylamine
  参考文献：
  名称：

  Synthesis and structural determination of (.+-.)-neplanocin F

  摘要：

  Neplanocin F (2), a minor constituent of the family of neplanocin antibiotics, was synthesized as a racemate in 12 steps from cyclopentenone 3/4, which in turn was available from D-ribonolactone. The carbocyclic ring of neplanocin F corresponds to the allylic rearranged isomer of the biologically active agent neplanocin A. Regiospecific reduction of the racemic cyclopentenone 3/4 and protection of the resulting alpha-alcohol as a benzyl ether 6 produced, after removal of the isopropylidene moiety, a compound (7) having allylic and homoallylic secondary alcohol functionalities. Differences in the reactivity of these two secondary alcohols were successfully manipulated to prepare the homoallylic substituted azide 14, which was then reduced and converted to the desired adenine ring by conventional methods. The spectral properties of the synthesized material [(+/-)-neplanocin F] were identical to those of the natural product, except for its lack of optical rotation. X-ray crystallographic analysis helped corroborate the structure. In contrast to its bioactive isomer, neoplanocin A, neplanocin F was devoid of cytotoxicity and in vitro antiviral activity.

  DOI：

  10.1021/jo00033a031