(2S,4R,5S,6R,7S)-7-(benzyloxy-diisopropyl-silanyloxy)-5-hydroxy-1-(4-methoxybenzyloxy)-2,4,6-trimethyl-nonan-3-one | 449174-12-3

• 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: (2S,4R,5S,6R,7S)-7-(benzyloxy-diisopropyl-silanyloxy)-5-hydroxy-1-(4-methoxybenzyloxy)-2,4,6-trimethyl-nonan-3-one
• CAS: 449174-12-3
• 化学式: C₃₃H₅₂O₆Si
• 分子量: 572.858
• InChiKey: CWMHASMZKCBCEU-DXOOBTRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.32
• 重原子数：
  40.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,4R,5S,6R,7S)-7-(benzyloxy-diisopropyl-silanyloxy)-5-hydroxy-1-(4-methoxybenzyloxy)-2,4,6-trimethyl-nonan-3-one 在 zinc(II) tetrahydroborate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 以91%的产率得到(2S,3R,4S,5R,6R,7S)-7-(benzyloxy-diisopropyl-silanyloxy)-1-(4-methoxy-benzyloxy)-2,4,6-trimethyl-nonane-3,5-diol
  参考文献：
  名称：

  Toward the Combinatorial Synthesis of Polyketide Libraries:  Asymmetric Aldol Reactions with α-Chiral Aldehydes on Solid Support

  摘要：

  [GRAPHIC]The viability of performing stereocontrolled aldol additions with a-chiral aldehydes attached by a silyl linker to a hydroxymethyl polystyrene resin is demonstrated for boron and titanium enolates. Subsequent ketone reduction and manipulation on the solid support leads to elaborate stereopentad sequences, as occur in 6-deoxyerythronolide B and discodermolide.

  DOI：

  10.1021/ol026046+
• 作为产物：
  描述：

  2,2,2-三氯代亚氨逐乙酸-4-甲氧基苄酯 在 titanium(IV) isopropylate 、 三氟甲磺酸 、 异丙基氯化镁 、 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.08h， 生成 (2S,4R,5S,6R,7S)-7-(benzyloxy-diisopropyl-silanyloxy)-5-hydroxy-1-(4-methoxybenzyloxy)-2,4,6-trimethyl-nonan-3-one
  参考文献：
  名称：

  Toward the Combinatorial Synthesis of Polyketide Libraries:  Asymmetric Aldol Reactions with α-Chiral Aldehydes on Solid Support

  摘要：

  [GRAPHIC]The viability of performing stereocontrolled aldol additions with a-chiral aldehydes attached by a silyl linker to a hydroxymethyl polystyrene resin is demonstrated for boron and titanium enolates. Subsequent ketone reduction and manipulation on the solid support leads to elaborate stereopentad sequences, as occur in 6-deoxyerythronolide B and discodermolide.

  DOI：

  10.1021/ol026046+