(E)-3-[2-methoxy-3-methoxymethoxymethyl-6-(trimethylsilanyl)pyridin-4-yl]pent-2-en-1-ol | 472958-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-[2-methoxy-3-methoxymethoxymethyl-6-(trimethylsilanyl)pyridin-4-yl]pent-2-en-1-ol
• 英文别名: (E)-3-[2-methoxy-3-(methoxymethoxymethyl)-6-trimethylsilylpyridin-4-yl]pent-2-en-1-ol
• CAS: 472958-63-7
• 化学式: C₁₇H₂₉NO₄Si
• 分子量: 339.507
• InChiKey: HIFNBFPYARJYBE-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-[2-methoxy-3-methoxymethoxymethyl-6-(trimethylsilanyl)pyridin-4-yl]pent-2-en-1-ol 在 4 A molecular sieve titanium(IV) isopropylate 、 叔丁基过氧化氢 、 sodium chlorite 、 lithium aluminium tetrahydride 、 disodium hydrogenphosphate 、 2-甲基-2-丁烯 、 L-(+)-酒石酸二乙酯 、 戴斯-马丁氧化剂 作用下， 以 乙醚 、 癸烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 21.0h， 生成 (-)-3-hydroxy-3-[2-methoxy-3-methoxymethoxymethyl-6-(trimethylsilanyl)pyridin-4-yl]pentanoic acid
  参考文献：
  名称：

  Asymmetric total synthesis of (20R)-homocamptothecin, substituted homocamptothecins and homosilatecans

  摘要：

  An efficient asymmetric synthesis of a key DE lactone pyridone intermediate in the synthesis of homocamptothecin is reported. The synthesis is scalable and features a Stille coupling and a Sharpless asymmetric epoxidation as the key steps. The key intermediate has been parleyed into homocamptothecin and an assortment of fluorinated homocamptothecins and homosilatecans (7-silylhomocamptothecins), thereby providing the first asymmetric entry to this important new class of antitumor agents. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00632-4
• 作为产物：
  描述：

  4-碘-2-甲氧基-6-三甲基硅烷基-3-吡啶甲醛 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 异丙基氯化镁 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 40.5h， 生成 (E)-3-[2-methoxy-3-methoxymethoxymethyl-6-(trimethylsilanyl)pyridin-4-yl]pent-2-en-1-ol
  参考文献：
  名称：

  Asymmetric total synthesis of (20R)-homocamptothecin, substituted homocamptothecins and homosilatecans

  摘要：

  An efficient asymmetric synthesis of a key DE lactone pyridone intermediate in the synthesis of homocamptothecin is reported. The synthesis is scalable and features a Stille coupling and a Sharpless asymmetric epoxidation as the key steps. The key intermediate has been parleyed into homocamptothecin and an assortment of fluorinated homocamptothecins and homosilatecans (7-silylhomocamptothecins), thereby providing the first asymmetric entry to this important new class of antitumor agents. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00632-4

文献信息

• Asymmetric total synthesis of (20R)-homocamptothecin, substituted homocamptothecins and homosilatecans
  作者：Ana E Gabarda、Wu Du、Thomas Isarno、Raghuram S Tangirala、Dennis P Curran

  DOI：10.1016/s0040-4020(02)00632-4

  日期：2002.8

  An efficient asymmetric synthesis of a key DE lactone pyridone intermediate in the synthesis of homocamptothecin is reported. The synthesis is scalable and features a Stille coupling and a Sharpless asymmetric epoxidation as the key steps. The key intermediate has been parleyed into homocamptothecin and an assortment of fluorinated homocamptothecins and homosilatecans (7-silylhomocamptothecins), thereby providing the first asymmetric entry to this important new class of antitumor agents. (C) 2002 Published by Elsevier Science Ltd.