6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz)-L-serinyl(P(O)(OBn)2)sulfamoyl]adenosine | 1356085-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz)-L-serinyl(P(O)(OBn)2)sulfamoyl]adenosine
• CAS: 1356085-33-0
• 化学式: C₅₀H₄₈N₇O₁₅PS
• 分子量: 1050.01
• InChiKey: XEHVMCGDCSBAHO-WHJDEGGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  74.0
• 可旋转键数：
  22.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  265.18
• 氢给体数：
  3.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz)-L-serinyl(P(O)(OBn)2)sulfamoyl]adenosine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 水 、 异丙醇 为溶剂， 70.0 ℃ 、5.0 MPa 条件下， 反应 2.0h， 以77%的产率得到((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl (O-phosphono-L-seryl)sulfamate
  参考文献：
  名称：

  Investigation, optimization and synthesis of sulfamoyloxy-linked aminoacyl-AMP analogues

  摘要：

  Aminoacyl-tRNA synthetases (aaRSs) constitute a family of enzymes that transfer amino acids to their corresponding tRNA molecules to form aminoacyl-tRNAs and have been validated as potential drug targets. Sulfamoyloxy-linked aminoacyl-AMP analogues are potent inhibitors of aaRSs. In this article, we report the synthesis of several new sulfamoyl analogues of as-AMP that up to now have been difficult or even impossible to prepare with current synthetic strategies. The developed synthetic strategy relies on performing the synthesis under neutral conditions followed by global deprotection using catalytic hydrogenation affording the desired 5'-0-(N-aminoacyl)sulfamoyladenosine compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.011
• 作为产物：
  描述：

  6-N-benzyloxycarbonyl-2',3'-O-benzylideneadenosine 在 4-二甲氨基吡啶 、 氨基磺酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz)-L-serinyl(P(O)(OBn)2)sulfamoyl]adenosine
  参考文献：
  名称：

  Investigation, optimization and synthesis of sulfamoyloxy-linked aminoacyl-AMP analogues

  摘要：

  Aminoacyl-tRNA synthetases (aaRSs) constitute a family of enzymes that transfer amino acids to their corresponding tRNA molecules to form aminoacyl-tRNAs and have been validated as potential drug targets. Sulfamoyloxy-linked aminoacyl-AMP analogues are potent inhibitors of aaRSs. In this article, we report the synthesis of several new sulfamoyl analogues of as-AMP that up to now have been difficult or even impossible to prepare with current synthetic strategies. The developed synthetic strategy relies on performing the synthesis under neutral conditions followed by global deprotection using catalytic hydrogenation affording the desired 5'-0-(N-aminoacyl)sulfamoyladenosine compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.011