(2S,3S,4S,5R,6R)-3-azido-4,5-dibenzoyloxy-6-[2-oxo-4-(2-trimethylsilylethoxycarbonylamino)pyrimidin-1-yl]oxane-2-carboxylic acid | 863871-04-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6R)-3-azido-4,5-dibenzoyloxy-6-[2-oxo-4-(2-trimethylsilylethoxycarbonylamino)pyrimidin-1-yl]oxane-2-carboxylic acid
• CAS: 863871-04-9
• 化学式: C₃₀H₃₂N₆O₁₀Si
• 分子量: 664.704
• InChiKey: XISWZPALFXVTOY-AMGAHSPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  185
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6R)-3-azido-4,5-dibenzoyloxy-6-[2-oxo-4-(2-trimethylsilylethoxycarbonylamino)pyrimidin-1-yl]oxane-2-carboxylic acid 、 叔丁氧羰酰基肌氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (2S,3S,4S,5R,6R)-3-[(R)-4-Amino-2-(2-methylamino-acetylamino)-butyrylamino]-6-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4,5-dihydroxy-tetrahydro-pyran-2-carboxylic acid amide
  参考文献：
  名称：

  An Efficient Synthesis of Gougerotin and Related Analogues Using Solid- and Solution-Phase Methodology

  摘要：

  [GRAPHIC]The first solid-phase synthesis of the natural product gougerotin has been accomplished. The synthetic route is versatile and allows for diversification at position C-4 of the heterocycle, C-6' of the sugar ring, and both residues of the peptidic moiety at N-4' in a parallel fashion.

  DOI：

  10.1021/ol0507322
• 作为产物：
  描述：

  4-acetylamino-1-(O⁶-acetyl-4-azido-O²,O³-dibenzoyl-β-D-4-deoxy-glucopyranosyl)-1H-pyrimidin-2-one 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 、 水 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 100.0h， 生成 (2S,3S,4S,5R,6R)-3-azido-4,5-dibenzoyloxy-6-[2-oxo-4-(2-trimethylsilylethoxycarbonylamino)pyrimidin-1-yl]oxane-2-carboxylic acid
  参考文献：
  名称：

  An Efficient Synthesis of Gougerotin and Related Analogues Using Solid- and Solution-Phase Methodology

  摘要：

  [GRAPHIC]The first solid-phase synthesis of the natural product gougerotin has been accomplished. The synthetic route is versatile and allows for diversification at position C-4 of the heterocycle, C-6' of the sugar ring, and both residues of the peptidic moiety at N-4' in a parallel fashion.

  DOI：

  10.1021/ol0507322

文献信息

• An Efficient Synthesis of Gougerotin and Related Analogues Using Solid- and Solution-Phase Methodology
  作者：Michael T. Migawa、Lisa M. Risen、Richard H. Griffey、Eric E. Swayze

  DOI：10.1021/ol0507322

  日期：2005.8.1

  [GRAPHIC]The first solid-phase synthesis of the natural product gougerotin has been accomplished. The synthetic route is versatile and allows for diversification at position C-4 of the heterocycle, C-6' of the sugar ring, and both residues of the peptidic moiety at N-4' in a parallel fashion.