{[(2R,5S)-5-(4-tert-Butoxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolan-2-ylmethoxycarbonylamino]-methyl}-phosphonic acid diethyl ester | 597581-72-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: {[(2R,5S)-5-(4-tert-Butoxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolan-2-ylmethoxycarbonylamino]-methyl}-phosphonic acid diethyl ester
• 英文别名: [(2R,5S)-5-[4-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxopyrimidin-1-yl]-1,3-oxathiolan-2-yl]methyl N-[[diethoxy(oxido)phosphaniumyl]methyl]carbamate
• CAS: 597581-72-1
• 化学式: C₁₉H₃₁N₄O₉PS
• 分子量: 522.516
• InChiKey: ZEPCIPBBAKLKFY-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  185
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  {[(2R,5S)-5-(4-tert-Butoxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolan-2-ylmethoxycarbonylamino]-methyl}-phosphonic acid diethyl ester 在 三甲基溴硅烷 、 sodium methylate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 生成 [[(2R,5S)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxycarbonylamino]methylphosphonic acid
  参考文献：
  名称：

  Are 5′-O-Carbamate-2′,3′-dideoxythiacytidine New Anti-HIV and Anti-HBV nucleoside Drugs or Prodrugs?

  摘要：

  In contrast to 5'-O-carbonate 3TC derivatives (23, 24), which are clearly 3TC prodrugs, the corresponding 3TC carbamates (15-21 and 25), found to be very stable compounds with respect to enzymatic hydrolysis (cellular lysates and culture cell media) and still active on both HIV-1 and HBV infected cells, may not be 3TC prodrugs. The antiviral properties as well as the mechanism of action of 3TC analogues have been studied and evaluated. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00496-7
• 作为产物：
  描述：

  拉米夫定 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 {[(2R,5S)-5-(4-tert-Butoxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolan-2-ylmethoxycarbonylamino]-methyl}-phosphonic acid diethyl ester
  参考文献：
  名称：

  Are 5′-O-Carbamate-2′,3′-dideoxythiacytidine New Anti-HIV and Anti-HBV nucleoside Drugs or Prodrugs?

  摘要：

  In contrast to 5'-O-carbonate 3TC derivatives (23, 24), which are clearly 3TC prodrugs, the corresponding 3TC carbamates (15-21 and 25), found to be very stable compounds with respect to enzymatic hydrolysis (cellular lysates and culture cell media) and still active on both HIV-1 and HBV infected cells, may not be 3TC prodrugs. The antiviral properties as well as the mechanism of action of 3TC analogues have been studied and evaluated. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00496-7