2, 3-O-isopropylidenefutalosine methyl ester | 1259953-76-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2, 3-O-isopropylidenefutalosine methyl ester
• CAS: 1259953-76-8
• 化学式: C₂₃H₂₄N₄O₇
• 分子量: 468.466
• InChiKey: VJQKUTWOZQXMSC-QTQZEZTPSA-N

物化性质

• 沸点：
  723.2±70.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  134.63
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2, 3-O-isopropylidenefutalosine methyl ester 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 0.5h， 以95%的产率得到futalosine methyl ester
  参考文献：
  名称：

  An efficient synthesis of futalosine

  摘要：

  Futalosine is a naturally occurring nucleoside comprised of an inosine core with a 3-carboxyphenyl methylene ketone functionality replacing the C-5' hydroxyl. Recent studies have shown that it is a key intermediate in an alternative biosynthetic pathway that generates menaquinone in a variety of bacterial species. Here we report the first synthesis of futalosine in seven steps from inosine in an overall 17% yield. This work will enable further studies on menaquinone biosynthesis in pathogenic bacteria. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.010
• 作为产物：
  描述：

  methyl 3-[3-[(3aR,4R,6R,6aR)-4-[1-(2,2-dimethylpropanoyloxymethyl)-6-oxopurin-9-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]propanoyl]benzoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以91%的产率得到2, 3-O-isopropylidenefutalosine methyl ester
  参考文献：
  名称：

  An efficient synthesis of futalosine

  摘要：

  Futalosine is a naturally occurring nucleoside comprised of an inosine core with a 3-carboxyphenyl methylene ketone functionality replacing the C-5' hydroxyl. Recent studies have shown that it is a key intermediate in an alternative biosynthetic pathway that generates menaquinone in a variety of bacterial species. Here we report the first synthesis of futalosine in seven steps from inosine in an overall 17% yield. This work will enable further studies on menaquinone biosynthesis in pathogenic bacteria. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.010