(1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-5-(acetyloxy)-2-cyclopenten-4-ol | 126798-08-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-5-(acetyloxy)-2-cyclopenten-4-ol
• CAS: 126798-08-1
• 化学式: C₂₂H₂₄O₅
• 分子量: 368.43
• InChiKey: XGNSVUDEYMSJAY-BDTNDASRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  溴甲苯 在 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.75h， 生成 (1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-5-(acetyloxy)-2-cyclopenten-4-ol
  参考文献：
  名称：

  （±）-neplanocin F的全合成

  摘要：

  （±）-Neplanocin F由外消旋体（/ ）分12步合成，该消旋体可从D-核糖内酯获得。

  DOI：

  10.1016/s0040-4039(01)80539-6

文献信息

• Synthesis and structural determination of (.+-.)-neplanocin F
  作者：Michael Bodenteich、Victor E. Marquez、Wendy H. Hallows、Barry M. Goldstein

  DOI：10.1021/jo00033a031

  日期：1992.3

  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.