[(2R,3S,5R)-3-Azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-phosphoramidic acid bis-(2,2,2-trichloro-ethyl) ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: [(2R,3S,5R)-3-Azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-phosphoramidic acid bis-(2,2,2-trichloro-ethyl) ester
• 英文别名: 1-[(2R,4S,5R)-4-azido-5-[[bis(2,2,2-trichloroethoxy)phosphorylamino]methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₁₄H₁₇Cl₆N₆O₆P
• 分子量: 609.017
• InChiKey: LTLCSGADLLUAGH-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-[[(2R,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl]isoindoline-1,3-dione 在 水 、 一水合肼 、 溶剂黄146 作用下， 反应 17.0h， 生成 [(2R,3S,5R)-3-Azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-phosphoramidic acid bis-(2,2,2-trichloro-ethyl) ester
  参考文献：
  名称：

  A rapid synthesis of some 5′-amino- nucleosides and nucleotides as potential antiviral compounds

  摘要：

  We describe a convenient method for the synthesis of 5'-amino-3'-azido-3',5'-dideoxythymidine and its conversion to a 5'-blocked phosphate derivative. The compounds are evaluated as inhibitors of HIV-1 in vitro, but prove to be poorly effective by comparison to their 5'-oxygen analogues. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0960-894x(96)00446-5

文献信息

• A rapid synthesis of some 5′-amino- nucleosides and nucleotides as potential antiviral compounds
  作者：Christopher McGuigan、Stephen Turner、Naheed Mahmood、Alan J Hay

  DOI：10.1016/0960-894x(96)00446-5

  日期：1996.10

  We describe a convenient method for the synthesis of 5'-amino-3'-azido-3',5'-dideoxythymidine and its conversion to a 5'-blocked phosphate derivative. The compounds are evaluated as inhibitors of HIV-1 in vitro, but prove to be poorly effective by comparison to their 5'-oxygen analogues. Copyright (C) 1996 Elsevier Science Ltd.