{2-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-phenyl}-carbamic acid tert-butyl ester | 169243-64-5

• 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: {2-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-phenyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]phenyl]carbamate
• CAS: 169243-64-5
• 化学式: C₂₀H₂₅N₃O₇
• 分子量: 419.434
• InChiKey: HQVNLVIXJDCIKY-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  137
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  {2-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-phenyl}-carbamic acid tert-butyl ester 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Hybridization properties of oligonucleotides bearing a tricyclic 2′-deoxycytidine analog based on a carbazole ring system

  摘要：

  A tricyclic carbazole-like 2'-deoxycytidine analog has been synthesized via a Stille biaryl coupling on 5-iodo-2'-deoxyuridine followed by cyclization. The carbazole nucleoside was incorporated in oligonucleotides (ONs) and shown to pair specifically with guanine. Duplexes resulting from the carbazole analog ONs and complementary RNA have elevated T(m)s especially when the carbazole nucleosides are clustered. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0040-4039(96)01016-7
• 作为产物：
  描述：

  碘苷 、 (2-三甲基stannanyl-苯基)-carbamic acid 叔丁酯 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到{2-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-phenyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Hybridization properties of oligonucleotides bearing a tricyclic 2′-deoxycytidine analog based on a carbazole ring system

  摘要：

  A tricyclic carbazole-like 2'-deoxycytidine analog has been synthesized via a Stille biaryl coupling on 5-iodo-2'-deoxyuridine followed by cyclization. The carbazole nucleoside was incorporated in oligonucleotides (ONs) and shown to pair specifically with guanine. Duplexes resulting from the carbazole analog ONs and complementary RNA have elevated T(m)s especially when the carbazole nucleosides are clustered. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0040-4039(96)01016-7

文献信息

• Hybridization properties of oligonucleotides bearing a tricyclic 2′-deoxycytidine analog based on a carbazole ring system
  作者：Mark D. Matteucci、Ulrike von Krosigk

  DOI：10.1016/0040-4039(96)01016-7

  日期：1996.7

  A tricyclic carbazole-like 2'-deoxycytidine analog has been synthesized via a Stille biaryl coupling on 5-iodo-2'-deoxyuridine followed by cyclization. The carbazole nucleoside was incorporated in oligonucleotides (ONs) and shown to pair specifically with guanine. Duplexes resulting from the carbazole analog ONs and complementary RNA have elevated T(m)s especially when the carbazole nucleosides are clustered. Copyright (C) 1996 Elsevier Science Ltd.