[(2S,3R,4S,6R)-2-[[(4S,5R,8R,9S,10S,11R,12R,15S,19R,21R,22R,24R)-9-[(2R,4R,5S,6S)-5-acetyloxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-5-ethyl-4,8,10,12,22,24-hexamethyl-2,7,23-trioxo-18-quinolin-3-yl-3,6,13,16-tetraoxa-1,17-diazatetracyclo[10.8.5.04,21.015,19]pentacos-17-en-11-yl]oxy]-4-(dimethylamino)-6-methyloxan-3-yl] acetate | 412048-03-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4S,6R)-2-[[(4S,5R,8R,9S,10S,11R,12R,15S,19R,21R,22R,24R)-9-[(2R,4R,5S,6S)-5-acetyloxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-5-ethyl-4,8,10,12,22,24-hexamethyl-2,7,23-trioxo-18-quinolin-3-yl-3,6,13,16-tetraoxa-1,17-diazatetracyclo[10.8.5.04,21.015,19]pentacos-17-en-11-yl]oxy]-4-(dimethylamino)-6-methyloxan-3-yl] acetate
• CAS: 412048-03-4
• 化学式: C₅₆H₈₀N₄O₁₆
• 分子量: 1065.27
• InChiKey: CKAXPPVJKDNDLG-OGIQIBSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  76
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  219
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S,6R)-2-[[(4S,5R,8R,9S,10S,11R,12R,15S,19R,21R,22R,24R)-9-[(2R,4R,5S,6S)-5-acetyloxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-5-ethyl-4,8,10,12,22,24-hexamethyl-2,7,23-trioxo-18-quinolin-3-yl-3,6,13,16-tetraoxa-1,17-diazatetracyclo[10.8.5.04,21.015,19]pentacos-17-en-11-yl]oxy]-4-(dimethylamino)-6-methyloxan-3-yl] acetate 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以56%的产率得到
  参考文献：
  名称：

  Regioselective Synthesis of Bifunctional Macrolides for Probing Ribosomal Binding

  摘要：

  [GRAPHICS]Bifunctional macrolides projecting an anchor group to the right or left spatial position of the lactone ring were synthesized. The regioselectivity of the key [3 + 2] cycloaddition process was controlled by the remote cladinose group attached to the C-3 position. These conformationally constrained molecules were employed as molecular probes to study the ribosomal binding sites of bifunctional macrolide antibiotics.

  DOI：

  10.1021/ol025554g
• 作为产物：
  描述：

  [(2S,3R,4S,6R)-2-[[(1S,2R,5R,6S,7S,8R,9R,11R,13R,14R)-6-[(2R,4R,5S,6S)-5-acetyloxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-2-ethyl-1,5,7,9,11,13-hexamethyl-4,12,16-trioxo-9-prop-2-enoxy-15-prop-2-enyl-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-8-yl]oxy]-4-(dimethylamino)-6-methyloxan-3-yl] acetate 在 Grubbs catalyst first generation 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 65.0h， 生成 [(2S,3R,4S,6R)-2-[[(4S,5R,8R,9S,10S,11R,12R,15S,19R,21R,22R,24R)-9-[(2R,4R,5S,6S)-5-acetyloxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-5-ethyl-4,8,10,12,22,24-hexamethyl-2,7,23-trioxo-18-quinolin-3-yl-3,6,13,16-tetraoxa-1,17-diazatetracyclo[10.8.5.04,21.015,19]pentacos-17-en-11-yl]oxy]-4-(dimethylamino)-6-methyloxan-3-yl] acetate
  参考文献：
  名称：

  Regioselective Synthesis of Bifunctional Macrolides for Probing Ribosomal Binding

  摘要：

  [GRAPHICS]Bifunctional macrolides projecting an anchor group to the right or left spatial position of the lactone ring were synthesized. The regioselectivity of the key [3 + 2] cycloaddition process was controlled by the remote cladinose group attached to the C-3 position. These conformationally constrained molecules were employed as molecular probes to study the ribosomal binding sites of bifunctional macrolide antibiotics.

  DOI：

  10.1021/ol025554g