1-[(2R,4S,5S)-4-azido-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]-6-ethylpyrimidine-2,4-dione | 178425-35-9

• 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: 1-[(2R,4S,5S)-4-azido-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]-6-ethylpyrimidine-2,4-dione
• CAS: 178425-35-9
• 化学式: C₂₇H₃₃N₅O₄Si
• 分子量: 519.676
• InChiKey: GMJVAXNNQDMPQY-JBRSBNLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  82.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5S)-4-azido-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]-6-ethylpyrimidine-2,4-dione 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以18%的产率得到1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-6-ethylpyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of an AZT-HEPT Hybrid and Homologous AzddU Derivatives.

  摘要：

  3'-Azido-2',3'-dideoxyuridines 6 and their corresponding cc anomers 5 were synthesized by condensation of silylated 6-alkyl and 5,6-dialkyl substituted uracils 2 with methyl 3-azido-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-alpha-beta-D-erythro-pentofuranoside (4). Compounds 5 and 6 were treated with tetrabutylammonium fluoride to obtain the deprotected nucleosides 7 and 8, respectively.

  DOI：

  10.3891/acta.chem.scand.50-0417
• 作为产物：
  描述：

  丙酰乙酸乙酯 在 硫酸氢铵 、 三氟甲磺酸三甲基硅酯 、 sodium ethanolate 、 氯乙酸 作用下， 以 乙腈 为溶剂， 反应 22.0h， 生成 1-[(2R,4S,5S)-4-azido-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]-6-ethylpyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of an AZT-HEPT Hybrid and Homologous AzddU Derivatives.

  摘要：

  3'-Azido-2',3'-dideoxyuridines 6 and their corresponding cc anomers 5 were synthesized by condensation of silylated 6-alkyl and 5,6-dialkyl substituted uracils 2 with methyl 3-azido-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-alpha-beta-D-erythro-pentofuranoside (4). Compounds 5 and 6 were treated with tetrabutylammonium fluoride to obtain the deprotected nucleosides 7 and 8, respectively.

  DOI：

  10.3891/acta.chem.scand.50-0417

文献信息

• Synthesis of an AZT-HEPT Hybrid and Homologous AzddU Derivatives.
  作者：Erik Larsen、Krzysztof Danel、Gitte B. Vaaben、Ali A. El-Emam、Erik B. Pedersen、Claus Nielsen、Shu Hai Zhao、Mauro I. Ciglic、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0417

  日期：——

  3'-Azido-2',3'-dideoxyuridines 6 and their corresponding cc anomers 5 were synthesized by condensation of silylated 6-alkyl and 5,6-dialkyl substituted uracils 2 with methyl 3-azido-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-alpha-beta-D-erythro-pentofuranoside (4). Compounds 5 and 6 were treated with tetrabutylammonium fluoride to obtain the deprotected nucleosides 7 and 8, respectively.