5-[N-(tert-butoxycarbonyl)]amino-4-cyanoacetyl-1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)imidazole | 310896-16-3

• 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-[N-(tert-butoxycarbonyl)]amino-4-cyanoacetyl-1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)imidazole
• 英文别名: tert-butyl N-[3-[(3aR,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-(2-cyanoacetyl)imidazol-4-yl]carbamate
• CAS: 310896-16-3
• 化学式: C₂₅H₄₀N₄O₇Si
• 分子量: 536.701
• InChiKey: ICMVWDSRGRKCPE-XLBJILASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-[N-(tert-butoxycarbonyl)]amino-4-cyanoacetyl-1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)imidazole 在 水 、 sodium carbonate 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 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 、 三乙胺 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 1.5h， 生成 5-[N-(tert-butoxycarbonyl)]amino-4-cyanoacetyl-1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)imidazole
  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