(5S,3S)-N-benzyloxycarbonyl-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-pyrrolidone | 832133-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5S,3S)-N-benzyloxycarbonyl-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-pyrrolidone
• 英文别名: benzyl (3S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(fluoromethyl)-2-oxopyrrolidine-1-carboxylate
• CAS: 832133-00-3
• 化学式: C₂₀H₃₀FNO₄Si
• 分子量: 395.546
• InChiKey: BYADOQCJPNKASR-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5S,3S)-N-benzyloxycarbonyl-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-pyrrolidone 在 吡啶 、 4-二甲氨基吡啶 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 benzyl (2R,3S,5S)-2-acetyloxy-5-tert-butyldimethylsilyloxymethyl-3-(monofluoromethyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of 2′,3′-dideoxy-2′-monofluoromethyl azanucleosides

  摘要：

  (2S,4S)-Methyl-N-tert-butoxycarbonyl-4-monofluoromethylpyroglutamate 6 was synthesized via a key dehydrofluorination followed by hydrogenation. Compound 6 was converted to (5S,3S)-N-benzyloxycarbonyl-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-pyrrolidone 12 over four steps in 62% yield, which was used as a precursor for the synthesis of 2',3'-dideoxy-2'-monofluoromethyl azanucleosides 17-18.

  DOI：

  10.1016/j.bmc.2004.09.040
• 作为产物：
  描述：

  1,2-Pyrrolidinedicarboxylic acid, 4-(fluoromethyl)-5-oxo-,1-(1,1-dimethylethyl) 2-methyl ester, (2S,4S)- 在 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 (5S,3S)-N-benzyloxycarbonyl-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-pyrrolidone
  参考文献：
  名称：

  Synthesis of 2′,3′-dideoxy-2′-monofluoromethyl azanucleosides

  摘要：

  (2S,4S)-Methyl-N-tert-butoxycarbonyl-4-monofluoromethylpyroglutamate 6 was synthesized via a key dehydrofluorination followed by hydrogenation. Compound 6 was converted to (5S,3S)-N-benzyloxycarbonyl-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-pyrrolidone 12 over four steps in 62% yield, which was used as a precursor for the synthesis of 2',3'-dideoxy-2'-monofluoromethyl azanucleosides 17-18.

  DOI：

  10.1016/j.bmc.2004.09.040

文献信息

• Synthesis of 2′,3′-dideoxy-2′-monofluoromethyl azanucleosides
  作者：Xiao-Long Qiup、Feng-Ling Qing

  DOI：10.1016/j.bmc.2004.09.040

  日期：2005.1

  (2S,4S)-Methyl-N-tert-butoxycarbonyl-4-monofluoromethylpyroglutamate 6 was synthesized via a key dehydrofluorination followed by hydrogenation. Compound 6 was converted to (5S,3S)-N-benzyloxycarbonyl-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-pyrrolidone 12 over four steps in 62% yield, which was used as a precursor for the synthesis of 2',3'-dideoxy-2'-monofluoromethyl azanucleosides 17-18.