methyl 3-[(E)-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]prop-2-enoyl]benzoate | 1259953-71-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: methyl 3-[(E)-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]prop-2-enoyl]benzoate
• CAS: 1259953-71-3
• 化学式: C₂₉H₃₂N₄O₉
• 分子量: 580.594
• InChiKey: DTMOZPSCMNBWSD-CBXQTYATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  148
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 3-[(E)-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]prop-2-enoyl]benzoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 以90%的产率得到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
  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：

  2-(3-methoxycarbonylphenyl)-2-oxoethyltriphenylphosphorane 、 2, 3-O-isopropylidene-1-N-pivaloyloxymethylinosine 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到methyl 3-[(E)-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]prop-2-enoyl]benzoate
  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

文献信息

• An efficient synthesis of futalosine
  作者：Xu Li、Martin E. Tanner

  DOI：10.1016/j.tetlet.2010.10.010

  日期：2010.12

  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.