(E)-3-[2-methoxy-3-methoxymethoxymethyl-6-(trimethylsilanyl)pyridin-4-yl]pent-2-enoic acid methyl ester | 472958-62-6

• 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-enoic acid methyl ester
• 英文别名: methyl (E)-3-[2-methoxy-3-(methoxymethoxymethyl)-6-trimethylsilylpyridin-4-yl]pent-2-enoate
• CAS: 472958-62-6
• 化学式: C₁₈H₂₉NO₅Si
• 分子量: 367.517
• InChiKey: SDLMFOMHQUAMKP-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-3-[2-methoxy-3-methoxymethoxymethyl-6-(trimethylsilanyl)pyridin-4-yl]pent-2-enoic acid methyl ester 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 、 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-enoic acid methyl ester
  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

• Intermediates and methods of preparation of intermediates in the enantiomeric synthesis of (20R)homocamptothecins and the enantiomeric synthesis of (20R)homocamptothecins
  申请人：——

  公开号：US20030073840A1

  公开（公告）日：2003-04-17

  A method of synthesizing a compound having the formula: 1 from a compound having the formula: 2 wherein R 1 is hydrogen, fluorine, chlorine or SiR 5 R 6 R 7 , wherein R 5 , R 6 , and R 7 are independently the same or different an alkyl group or an aryl group, R 2 is an alkyl group, R 3 is a protecting group, R 4 is an alkyl group, an allyl group, a propargyl group —CO 2 H, or a benzyl group, R 8 is —CO 2 R 10 , wherein R 10 is an alkyl group or an aryl group, X 1 is OH and X 2 is H, includes the step of exposing compound (III) to at least one of an organic acid or an inorganic acid. A compound has the general formula (III).

  一种合成具有公式1的化合物的方法：从具有公式2的化合物开始，其中R1是氢、氟、氯或SiR5R6R7，其中R5、R6和R7分别是相同或不同的烷基或芳基，R2是烷基，R3是保护基，R4是烷基、烯丙基、丙炔基-CO2H或苄基，R8是-CO2R10，其中R10是烷基或芳基，X1是OH，X2是H，包括将化合物（III）暴露于有机酸或无机酸之一的步骤。化合物具有通用公式（III）。
• 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.