(1S,3S,4S,5R)-1,6:7,8-bis-O-isopropylidene-3-(4'-nitrobenzoyl)-1,4,5-tris(hydroxymethyl)cyclopentane-1,3-diol | 442906-69-6

• 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: (1S,3S,4S,5R)-1,6:7,8-bis-O-isopropylidene-3-(4'-nitrobenzoyl)-1,4,5-tris(hydroxymethyl)cyclopentane-1,3-diol
• CAS: 442906-69-6
• 化学式: C₂₁H₂₇NO₈
• 分子量: 421.447
• InChiKey: NFUIYSHXKCSXPU-MXTNKPTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  106.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (1S,3S,4S,5R)-1,6:7,8-bis-O-isopropylidene-3-(4'-nitrobenzoyl)-1,4,5-tris(hydroxymethyl)cyclopentane-1,3-diol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以96%的产率得到(1S,3S,4S,5R)-1,6:7,8-bis-O-isopropylidene-1,4,5-tris(hydroxymethyl)cyclopentane-1,3-diol
  参考文献：
  名称：

  SYNTHESIS OF NOVEL HYDROXYMETHYL SUBSTITUTED ANALOGUES RELATED TO CARBOVIR AND NEPLANOCIN A

  摘要：

  Two enantiomerically pure hydroxymethyl substituted cyclopentene nucleoside analogues (42 and 53) related to carbovir and neplanocin A., respectively, were prepared from the chiral pool of iridoid glucosides. In addition two saturated hydroxymethylated analogues (44 and 45) were obtained from a protected intermediate.

  DOI：

  10.1081/ncn-120006528
• 作为产物：
  描述：

  (5S,7R,8S,9R)-8,9-bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxaspiro[4.4]nonan-7-ol 在 4-甲基苯磺酸吡啶 、 copper(II) sulfate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 18.0h， 生成 (1S,3S,4S,5R)-1,6:7,8-bis-O-isopropylidene-3-(4'-nitrobenzoyl)-1,4,5-tris(hydroxymethyl)cyclopentane-1,3-diol
  参考文献：
  名称：

  SYNTHESIS OF NOVEL HYDROXYMETHYL SUBSTITUTED ANALOGUES RELATED TO CARBOVIR AND NEPLANOCIN A

  摘要：

  Two enantiomerically pure hydroxymethyl substituted cyclopentene nucleoside analogues (42 and 53) related to carbovir and neplanocin A., respectively, were prepared from the chiral pool of iridoid glucosides. In addition two saturated hydroxymethylated analogues (44 and 45) were obtained from a protected intermediate.

  DOI：

  10.1081/ncn-120006528