5-amino-4-cyanoacetyl-1-β-D-ribofuranosylimidazole | 310896-19-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: 5-amino-4-cyanoacetyl-1-β-D-ribofuranosylimidazole
• 英文别名: 3-[5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazol-4-yl]-3-oxopropanenitrile
• CAS: 310896-19-6
• 化学式: C₁₁H₁₄N₄O₅
• 分子量: 282.256
• InChiKey: TULSCEGESDMVAB-PNHWDRBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  155
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-amino-4-cyanoacetyl-1-β-D-ribofuranosylimidazole 在 水 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以65%的产率得到5-amino-3-(β-D-ribofuranosyl)imidazo[4,5-b]pyridin-7-one
  参考文献：
  名称：

  Nucleosides and Nucleotides. Part 207: Studies in the Chemical Conversion of the 4-Carboxamide Group of 5-Amino-1-β-d-ribofuranosylimidazole-4-carboxamide (AICA-Riboside). Application for the Synthesis of 1-Deazaguanosine

  摘要：

  A mild and versatile chemical conversion of the 4-carboxamide group of 5-amino-1-beta-D-ribofuranosylimidazole-4-carboxamide (AICA-riboside) is described. The reaction of protected AICA-riboside with di-tert-butyl dicarbonate gave 5-[N,N-di-(tert-butoxycarbonyl)]-amino-1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-beta-D-ribofurnaosyl)imidazole-4-[N,N-di-(tert-butoxycarbonyl)]carboxamide in 71% yield. The resulting tetraBoc derivative was treated with sodium methoxide, benzylamine, or acetonitrile anion to give the corresponding methyl ester, N-benzylcarboxamide, or cyanoacetyl products. The 4-cyanoacetylimidazole derivative was converted into 1-deazaguanosine via an intramolecular cyclization. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00712-2
• 作为产物：
  描述：

  5-amino-1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)imidazole-4-carboxamide 在 4-二甲氨基吡啶 、 正丁基锂 、 水 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 13.5h， 生成 5-amino-4-cyanoacetyl-1-β-D-ribofuranosylimidazole
  参考文献：
  名称：

  Nucleosides and Nucleotides. Part 207: Studies in the Chemical Conversion of the 4-Carboxamide Group of 5-Amino-1-β-d-ribofuranosylimidazole-4-carboxamide (AICA-Riboside). Application for the Synthesis of 1-Deazaguanosine

  摘要：

  A mild and versatile chemical conversion of the 4-carboxamide group of 5-amino-1-beta-D-ribofuranosylimidazole-4-carboxamide (AICA-riboside) is described. The reaction of protected AICA-riboside with di-tert-butyl dicarbonate gave 5-[N,N-di-(tert-butoxycarbonyl)]-amino-1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-beta-D-ribofurnaosyl)imidazole-4-[N,N-di-(tert-butoxycarbonyl)]carboxamide in 71% yield. The resulting tetraBoc derivative was treated with sodium methoxide, benzylamine, or acetonitrile anion to give the corresponding methyl ester, N-benzylcarboxamide, or cyanoacetyl products. The 4-cyanoacetylimidazole derivative was converted into 1-deazaguanosine via an intramolecular cyclization. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00712-2

文献信息

• Nucleosides and Nucleotides. Part 207: Studies in the Chemical Conversion of the 4-Carboxamide Group of 5-Amino-1-β-d-ribofuranosylimidazole-4-carboxamide (AICA-Riboside). Application for the Synthesis of 1-Deazaguanosine
  作者：Naoshi Kojima、Noriaki Minakawa、Akira Matsuda

  DOI：10.1016/s0040-4020(00)00712-2

  日期：2000.9

  A mild and versatile chemical conversion of the 4-carboxamide group of 5-amino-1-beta-D-ribofuranosylimidazole-4-carboxamide (AICA-riboside) is described. The reaction of protected AICA-riboside with di-tert-butyl dicarbonate gave 5-[N,N-di-(tert-butoxycarbonyl)]-amino-1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-beta-D-ribofurnaosyl)imidazole-4-[N,N-di-(tert-butoxycarbonyl)]carboxamide in 71% yield. The resulting tetraBoc derivative was treated with sodium methoxide, benzylamine, or acetonitrile anion to give the corresponding methyl ester, N-benzylcarboxamide, or cyanoacetyl products. The 4-cyanoacetylimidazole derivative was converted into 1-deazaguanosine via an intramolecular cyclization. (C) 2000 Elsevier Science Ltd. All rights reserved.