4-(1,2:3,4-di-O-isopropylidene-D-xylo-1,2,3,4-tetrahydroxybutyl)-2-methylpyrimidine | 876861-56-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(1,2:3,4-di-O-isopropylidene-D-xylo-1,2,3,4-tetrahydroxybutyl)-2-methylpyrimidine
• 英文别名: 4-[(4S,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methylpyrimidine
• CAS: 876861-56-2
• 化学式: C₁₅H₂₂N₂O₄
• 分子量: 294.351
• InChiKey: LKIFXPDYUOKXIC-AGIUHOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(1,2:3,4-di-O-isopropylidene-D-xylo-1,2,3,4-tetrahydroxybutyl)-2-methylpyrimidine 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以80%的产率得到4-(D-xylo-1,2,3,4-tetrahydroxybutyl)-2-methylpyrimidine
  参考文献：
  名称：

  Syntheses of Acyclo‐C‐nucleoside Analogs from 2,3:4,5‐Di‐O‐isopropylidene‐D‐xylose

  摘要：

  Treatment of 1,2-dideoxy-4,5:6,7-di- O -isopropylidene-D- xylo -hept-1-yn-3-uloses 4a,b with hydrazine hydrate and amidines yielded the 3-(1,2:3,4-di- O -isopropylidene-D- xylo -1,2,3,4-tetrahydroxy-butyl)-5-phenyl-1 H (2 H )-pyrazole 5 and the substituted 4-(1,2:3,4-di- O -isopropylidene-D- xylo -1,2,3,4-tetrahydroxy-butyl)pyrimidines 7a-f, respectively. Reaction of 4a,b with 2-amino-benzimidazol afforded the 2-(1,2:3,4-di- O -isopropylidene-D- xylo -1,2,3,4-tetrahydroxy-butyl)benzo[4,5]imidazo[1,2- a ]pyrimidines 9a,b. Compound 4a and 5-amino-pyrazole-4-carbonic acid derivatives yielded the 5-(1,2:3,4-di- O -isopropylidene-D- xylo -1,2,3,4-tetrahydroxy-butyl)pyrazolo[1,5- a ]pyrimidines 11a-d. Deprotection of pyrazole 5, pyrimidine 7a, and pyrazolo[1,5- a ]pyrimidine 11b yielded the acyclo- C -nucleosides 6, 8, and 12, respectively.

  DOI：

  10.1080/07328300500388693
• 作为产物：
  描述：

  2,3:4,5-二-O-(1-甲基乙亚基)-D-木糖 在 乙酸酐 、 sodium carbonate 、 二甲基亚砜 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 29.0h， 生成 4-(1,2:3,4-di-O-isopropylidene-D-xylo-1,2,3,4-tetrahydroxybutyl)-2-methylpyrimidine
  参考文献：
  名称：

  Syntheses of Acyclo‐C‐nucleoside Analogs from 2,3:4,5‐Di‐O‐isopropylidene‐D‐xylose

  摘要：

  Treatment of 1,2-dideoxy-4,5:6,7-di- O -isopropylidene-D- xylo -hept-1-yn-3-uloses 4a,b with hydrazine hydrate and amidines yielded the 3-(1,2:3,4-di- O -isopropylidene-D- xylo -1,2,3,4-tetrahydroxy-butyl)-5-phenyl-1 H (2 H )-pyrazole 5 and the substituted 4-(1,2:3,4-di- O -isopropylidene-D- xylo -1,2,3,4-tetrahydroxy-butyl)pyrimidines 7a-f, respectively. Reaction of 4a,b with 2-amino-benzimidazol afforded the 2-(1,2:3,4-di- O -isopropylidene-D- xylo -1,2,3,4-tetrahydroxy-butyl)benzo[4,5]imidazo[1,2- a ]pyrimidines 9a,b. Compound 4a and 5-amino-pyrazole-4-carbonic acid derivatives yielded the 5-(1,2:3,4-di- O -isopropylidene-D- xylo -1,2,3,4-tetrahydroxy-butyl)pyrazolo[1,5- a ]pyrimidines 11a-d. Deprotection of pyrazole 5, pyrimidine 7a, and pyrazolo[1,5- a ]pyrimidine 11b yielded the acyclo- C -nucleosides 6, 8, and 12, respectively.

  DOI：

  10.1080/07328300500388693

文献信息

• Syntheses of Acyclo‐<i>C</i>‐nucleoside Analogs from 2,3:4,5‐Di‐<i>O</i>‐isopropylidene‐<scp>D</scp>‐xylose
  作者：Iran Otero、Karen Methling、Holger Feist、Manfred Michalik、José Quincoces、Helmut Reinke、Klaus Peseke

  DOI：10.1080/07328300500388693

  日期：2005.11.1

  Treatment of 1,2-dideoxy-4,5:6,7-di- O -isopropylidene-D- xylo -hept-1-yn-3-uloses 4a,b with hydrazine hydrate and amidines yielded the 3-(1,2:3,4-di- O -isopropylidene-D- xylo -1,2,3,4-tetrahydroxy-butyl)-5-phenyl-1 H (2 H )-pyrazole 5 and the substituted 4-(1,2:3,4-di- O -isopropylidene-D- xylo -1,2,3,4-tetrahydroxy-butyl)pyrimidines 7a-f, respectively. Reaction of 4a,b with 2-amino-benzimidazol afforded the 2-(1,2:3,4-di- O -isopropylidene-D- xylo -1,2,3,4-tetrahydroxy-butyl)benzo[4,5]imidazo[1,2- a ]pyrimidines 9a,b. Compound 4a and 5-amino-pyrazole-4-carbonic acid derivatives yielded the 5-(1,2:3,4-di- O -isopropylidene-D- xylo -1,2,3,4-tetrahydroxy-butyl)pyrazolo[1,5- a ]pyrimidines 11a-d. Deprotection of pyrazole 5, pyrimidine 7a, and pyrazolo[1,5- a ]pyrimidine 11b yielded the acyclo- C -nucleosides 6, 8, and 12, respectively.