methyl (2S)-2-[[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl-[(2-methylpropan-2-yl)oxycarbonyl]sulfamoyl]amino]-3-phenylpropanoate | 172945-95-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-2-[[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl-[(2-methylpropan-2-yl)oxycarbonyl]sulfamoyl]amino]-3-phenylpropanoate
• CAS: 172945-95-8
• 化学式: C₂₅H₃₄N₄O₁₀S
• 分子量: 582.632
• InChiKey: FHBHKJAMTUAPTO-VNTMZGSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  189
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl-[(2-methylpropan-2-yl)oxycarbonyl]sulfamoyl]amino]-3-phenylpropanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以71%的产率得到methyl (2S)-2-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methylsulfamoylamino]-3-phenylpropanoate
  参考文献：
  名称：

  Nucleopeptidic Bioconjugates Containing a Sulfamide Bridge: LinkageviatheMitsunobuReaction

  摘要：

  The synthesis of compounds connecting unprotected 2'-deoxyribonucleosides (T,dC,dG,dA) with N-Boc sulfamoyl derivatives of natural aminoacid esters (Phe, Asp) was carried out by Mitsunobu reaction, using regiospecific coupling. The created link was a priori non-hydrolyzable in biological conditions.

  DOI：

  10.1080/15257779508009757
• 作为产物：
  描述：

  N-(叔丁氧基羰基)磺酰氯 在 三乙胺 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 methyl (2S)-2-[[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl-[(2-methylpropan-2-yl)oxycarbonyl]sulfamoyl]amino]-3-phenylpropanoate
  参考文献：
  名称：

  Nucleopeptidic Bioconjugates Containing a Sulfamide Bridge: LinkageviatheMitsunobuReaction

  摘要：

  The synthesis of compounds connecting unprotected 2'-deoxyribonucleosides (T,dC,dG,dA) with N-Boc sulfamoyl derivatives of natural aminoacid esters (Phe, Asp) was carried out by Mitsunobu reaction, using regiospecific coupling. The created link was a priori non-hydrolyzable in biological conditions.

  DOI：

  10.1080/15257779508009757

文献信息

• Nucleopeptidic Bioconjugates Containing a Sulfamide Bridge: Linkage<i>via</i>the<i>Mitsunobu</i>Reaction
  作者：Marc Critonl、Georges Dewyntert、Nourreddine Aouf、Jean-Louis Montero、Jean-Louis Imbach

  DOI：10.1080/15257779508009757

  日期：1995.10

  The synthesis of compounds connecting unprotected 2'-deoxyribonucleosides (T,dC,dG,dA) with N-Boc sulfamoyl derivatives of natural aminoacid esters (Phe, Asp) was carried out by Mitsunobu reaction, using regiospecific coupling. The created link was a priori non-hydrolyzable in biological conditions.