(2R,3R,4S,5R,6S,7R)-3,5-isopropylidendioxy-1-(4-methoxy-benzyloxy)-2,4,6-trimethylnonan-7-ol | 449174-11-2

• 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: (2R,3R,4S,5R,6S,7R)-3,5-isopropylidendioxy-1-(4-methoxy-benzyloxy)-2,4,6-trimethylnonan-7-ol
• 英文别名: (2S,3R)-2-[(4R,5S,6R)-6-[(2R)-1-[(4-methoxyphenyl)methoxy]propan-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl]pentan-3-ol
• CAS: 449174-11-2
• 化学式: C₂₃H₃₈O₅
• 分子量: 394.552
• InChiKey: MZIKGVCGYDQPCC-QXVZDWRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S,7R)-3,5-isopropylidendioxy-1-(4-methoxy-benzyloxy)-2,4,6-trimethylnonan-7-ol 在 戴斯-马丁氧化剂 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 1.5h， 以88%的产率得到(2R,3R,4S,5S,6R)-3,5-isopropylidendioxy-1-(4-methoxy-benzyloxy)-2,4,6-trimethylnonan-7-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+
• 作为产物：
  描述：

  (R)-methyl 3-((4-methoxybenzyl)oxy)-2-methylpropanoate 在 吡啶 、 锂硼氢 、 samarium diiodide 、 氯代二环己基硼烷 、 异丙基氯化镁 、 4-甲基苯磺酸吡啶 、 氟化氢吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 38.75h， 生成 (2R,3R,4S,5R,6S,7R)-3,5-isopropylidendioxy-1-(4-methoxy-benzyloxy)-2,4,6-trimethylnonan-7-ol
  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+

文献信息

• Toward the Combinatorial Synthesis of Polyketide Libraries:  Asymmetric Aldol Reactions with α-Chiral Aldehydes on Solid Support
  作者：Ian Paterson、Taoues Temal-Laïb

  DOI：10.1021/ol026046+

  日期：2002.7.1

  [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.