1-deoxy-1-phenyl-D-ribitol | 138385-34-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-deoxy-1-phenyl-D-ribitol
• 英文别名: (2R,3S,4S)-5-phenylpentane-1,2,3,4-tetrol
• CAS: 138385-34-9
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: BZQIEZTUMMBKKT-AXFHLTTASA-N

物化性质

• 沸点：
  460.9±45.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1-deoxy-1-phenyl-D-ribitol 在 吡啶 作用下， 反应 14.0h， 以65%的产率得到D-Ribitol, 1-deoxy-1-phenyl-, tetraacetate
  参考文献：
  名称：

  Synthesis and cytotoxic activity of C-glycosidic nicotinamide riboside analogs

  摘要：

  The C-glycosidic nicotinamide riboside analogue (2) was prepared by reaction of ribonolactone 24 with the lithiated oxazoline 19 followed by triethylsilane reduction to 26 and deprotection. Selective phosphorylation to the pseudonucleotide 34 was effected via the isopropylidene compound 33. In contrast to the benzoic acid riboside (28) the benzamide riboside (2) showed extremely high cytotoxicity at nanomolar concentrations to S49.1 lymphoma cells but only slightly increased dexamethasone toxicity.

  DOI：

  10.1021/jm00081a012
• 作为产物：
  描述：

  2,3,5-三-O-(苯基甲基)-D-呋喃核糖 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 苯 为溶剂， 20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 30.0h， 生成 1-deoxy-1-phenyl-D-ribitol
  参考文献：
  名称：

  Synthesis and cytotoxic activity of C-glycosidic nicotinamide riboside analogs

  摘要：

  The C-glycosidic nicotinamide riboside analogue (2) was prepared by reaction of ribonolactone 24 with the lithiated oxazoline 19 followed by triethylsilane reduction to 26 and deprotection. Selective phosphorylation to the pseudonucleotide 34 was effected via the isopropylidene compound 33. In contrast to the benzoic acid riboside (28) the benzamide riboside (2) showed extremely high cytotoxicity at nanomolar concentrations to S49.1 lymphoma cells but only slightly increased dexamethasone toxicity.

  DOI：

  10.1021/jm00081a012

文献信息

• Synthesis and cytotoxic activity of C-glycosidic nicotinamide riboside analogs
  作者：Karsten Krohn、Heidi Heins、Klaus Wielckens

  DOI：10.1021/jm00081a012

  日期：1992.2

  The C-glycosidic nicotinamide riboside analogue (2) was prepared by reaction of ribonolactone 24 with the lithiated oxazoline 19 followed by triethylsilane reduction to 26 and deprotection. Selective phosphorylation to the pseudonucleotide 34 was effected via the isopropylidene compound 33. In contrast to the benzoic acid riboside (28) the benzamide riboside (2) showed extremely high cytotoxicity at nanomolar concentrations to S49.1 lymphoma cells but only slightly increased dexamethasone toxicity.