3-(benzyloxymethyl)-1-[(Z)-2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-formamido-β-D-ribo-pentofuranosyl]uracil | 1384963-27-2

• 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: 3-(benzyloxymethyl)-1-[(Z)-2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-formamido-β-D-ribo-pentofuranosyl]uracil
• CAS: 1384963-27-2
• 化学式: C₃₀H₄₇N₃O₇Si₂
• 分子量: 617.89
• InChiKey: QBPAKIIEQQYSBV-SHUXOKDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  110.02
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3-(benzyloxymethyl)-1-[(Z)-2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-formamido-β-D-ribo-pentofuranosyl]uracil 在 三光气 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 52.33h， 生成
  参考文献：
  名称：

  Synthesis of pacidamycin analogues via an Ugi-multicomponent reaction

  摘要：

  The second-generation synthesis of 3'-hydroxypacidamycin D (2) has been accomplished via an Ugi-four component reaction at a late stage of the synthesis. This approach provided ready access to a range of analogues including diastereomers of the diaminobutylic acid residue and hybrid-type analogues of mureidomycins. Biological evaluations of these analogues indicated that the stereochemistry at the diaminobutylic acid residue has a crucial impact on both the MraY biochemical inhibition and whole-cell anti-bacterial activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.050
• 作为产物：
  描述：

  (Z)-3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-5-iodo-β-D-ribopentofuranosyl]uracil 、 formamide 在 copper(l) iodide 、 caesium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以90%的产率得到3-(benzyloxymethyl)-1-[(Z)-2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-formamido-β-D-ribo-pentofuranosyl]uracil
  参考文献：
  名称：

  Synthesis of pacidamycin analogues via an Ugi-multicomponent reaction

  摘要：

  The second-generation synthesis of 3'-hydroxypacidamycin D (2) has been accomplished via an Ugi-four component reaction at a late stage of the synthesis. This approach provided ready access to a range of analogues including diastereomers of the diaminobutylic acid residue and hybrid-type analogues of mureidomycins. Biological evaluations of these analogues indicated that the stereochemistry at the diaminobutylic acid residue has a crucial impact on both the MraY biochemical inhibition and whole-cell anti-bacterial activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.050