Imidazole-1-carboxylic acid [(2S,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-amide | 287727-89-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: Imidazole-1-carboxylic acid [(2S,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-amide
• 英文别名: N-[(2S,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]imidazole-1-carboxamide
• CAS: 287727-89-3
• 化学式: C₂₀H₃₁N₅O₅Si
• 分子量: 449.582
• InChiKey: BJPUFZOBFVNOSB-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Imidazole-1-carboxylic acid [(2S,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-amide 在 氟化氢吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-[2-[(E)-[(2R,3S,4R,5S,7R,9R,10R,11S,12S,13R)-10-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,9-trihydroxy-12-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-14-oxo-oxacyclotetradec-6-ylidene]amino]oxyethyl]-3-[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]urea
  参考文献：
  名称：

  Clarithromycin–adenine and related conjugates

  摘要：

  Macrolide-nucleoside and macrolide-nucleobase conjugates (chimeras) have been synthesised by linking erythromycin A oxime derivatives and clarithromycin C11,C12-oxazolidinone derivatives with 3'-amino-3'-deoxythymidine or adenine through different spacers; clarithromycin-adenine conjugate 16a is the most active species against Micrococcus luteus. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.01.079
• 作为产物：
  描述：

  N,N'-羰基二咪唑 、 5'-O-(tert-butyldimethylsilyl)-3'-amino-3'-deoxythymidine 以 二氯甲烷 为溶剂， 以91%的产率得到Imidazole-1-carboxylic acid [(2S,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-amide
  参考文献：
  名称：

  大环内酯与核碱基或核苷的杂种

  摘要：

  报道了红霉素A衍生物和核碱基（尿嘧啶和胸腺嘧啶）或胸苷衍生的核苷的杂合体/结合物/嵌合体的一些实例。已经研究了接头和反应条件，以避免大环内酯部分的降解（糖苷水解，环裂解，脱水等）。

  DOI：

  10.1016/s0040-4039(00)00417-2

文献信息

• Hybrids of macrolides and nucleobases or nucleosides
  作者：Anna M Costa、Jaume Vilarrasa

  DOI：10.1016/s0040-4039(00)00417-2

  日期：2000.4

  examples of hybrids/conjugates/chimeras of erythromycin A derivatives and nucleobases (uracil and thymine) or thymidine-derived nucleosides are reported. Linkers and reaction conditions have been investigated to avoid the degradation of the macrolide moiety (glycoside hydrolysis, ring cleavage, dehydration, etc.).

  报道了红霉素A衍生物和核碱基（尿嘧啶和胸腺嘧啶）或胸苷衍生的核苷的杂合体/结合物/嵌合体的一些实例。已经研究了接头和反应条件，以避免大环内酯部分的降解（糖苷水解，环裂解，脱水等）。
• Clarithromycin–adenine and related conjugates
  作者：Jorge Esteban、Anna M. Costa、M. Carmen Cruzado、Montserrat Faja、Pilar García、Jaume Vilarrasa

  DOI：10.1016/j.tetlet.2006.01.079

  日期：2006.3

  Macrolide-nucleoside and macrolide-nucleobase conjugates (chimeras) have been synthesised by linking erythromycin A oxime derivatives and clarithromycin C11,C12-oxazolidinone derivatives with 3'-amino-3'-deoxythymidine or adenine through different spacers; clarithromycin-adenine conjugate 16a is the most active species against Micrococcus luteus. (c) 2006 Elsevier Ltd. All rights reserved.