N-[2-pivaloyloxy-1-(pivaloyloxymethyl)ethyl]-methanesulfonamide | 740801-48-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-[2-pivaloyloxy-1-(pivaloyloxymethyl)ethyl]-methanesulfonamide
• 英文别名: [3-(2,2-Dimethylpropanoyloxy)-2-(methanesulfonamido)propyl] 2,2-dimethylpropanoate
• CAS: 740801-48-3
• 化学式: C₁₄H₂₇NO₆S
• 分子量: 337.437
• InChiKey: YFINJIDDFVWIJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  98.77
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-[2-pivaloyloxy-1-(pivaloyloxymethyl)ethyl]-methanesulfonamide 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 96.0h， 生成 2,2-Dimethyl-propionic acid 2-[(4-benzoylamino-2-oxo-2H-pyrimidin-1-ylmethyl)-methanesulfonyl-amino]-3-(2,2-dimethyl-propionyloxy)-propyl ester
  参考文献：
  名称：

  Facile synthesis of acyclic azanucleosides from N -pivaloyloxymethyl amides and sulfonamides: synthesis of aza-analogues of Ganciclovir

  摘要：

  N-Pivaloyloxymethyl amides and sulfonamides, readily available from N-alkylation of both amides and sulfonamides with commercial chloromethyl pivaloate, were converted into acyclic azanucleosides via a one-pot base silylation/nucleoside coupling procedure. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.042
• 作为产物：
  描述：

  三甲基乙酰氯 、 N-(2-Hydroxy-1-hydroxymethyl-ethyl)-methanesulfonamide 在 吡啶 作用下， 反应 24.0h， 以42%的产率得到N-[2-pivaloyloxy-1-(pivaloyloxymethyl)ethyl]-methanesulfonamide
  参考文献：
  名称：

  Facile synthesis of acyclic azanucleosides from N -pivaloyloxymethyl amides and sulfonamides: synthesis of aza-analogues of Ganciclovir

  摘要：

  N-Pivaloyloxymethyl amides and sulfonamides, readily available from N-alkylation of both amides and sulfonamides with commercial chloromethyl pivaloate, were converted into acyclic azanucleosides via a one-pot base silylation/nucleoside coupling procedure. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.042

文献信息

• Synthesis of aza-analogues of Ganciclovir
  作者：Mariola Koszytkowska-Stawińska、Wojciech Sas、Erik De Clercq

  DOI：10.1016/j.tet.2006.08.072

  日期：2006.10

  Aza-analogues of ganciclovir have been prepared via coupling of nucleobases with N-[2-pivaloyloxy-1-(pivaloyloxymethyl)ethyl] methanesulfonamide or 3-mesyl-4-(benzoyloxymethyl)-1,3-oxazolidine. (c) 2006 Elsevier Ltd. All rights reserved.