(2S,3S,4S)-4-methoxy-3-(4-methoxybenzyloxy)-2-methylhex-5-enal | 910215-27-9

• 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,3S,4S)-4-methoxy-3-(4-methoxybenzyloxy)-2-methylhex-5-enal
• 英文别名: (2S,3S,4S)-4-methoxy-3-[(4-methoxyphenyl)methoxy]-2-methylhex-5-enal
• CAS: 910215-27-9
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: PDTBXKACIIJAIX-KCXAZCMYSA-N

物化性质

• 沸点：
  384.7±42.0 °C(predicted)
• 密度：
  1.038±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-4-methoxy-3-(4-methoxybenzyloxy)-2-methylhex-5-enal 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 吡啶 、 2,4,6-三氯苯甲酰氯 、 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 28.25h， 生成 (9S,10S,11R)-9-methoxy-10-(4-methoxybenzyloxy)-11,13-dimethyloxacyclotetradeca-3,7,12-trien-2-one
  参考文献：
  名称：

  A convergent synthesis of the macrolide core of migrastatin

  摘要：

  We describe an efficient synthesis of the 14-membered macrolide core 2 of migrastatin via key intermediate 3 employing a diastereoselective aldol condensation, Lewis acid mediated diastereoselective addition and an exclusive (Z)-olefination sequence. Yamaguchi esterification of the key intermediate 3 followed by ring-closing metathesis (RCM) produced macrolide 2 with high selectivity and good yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.082
• 作为产物：
  描述：

  tert-butyl[(2R,3S,4S)-4-methoxy-3-(4-methoxybenzyloxy)-2-methylhex-5-enyloxy]dimethylsilane 在 四丁基氟化铵 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.67h， 生成 (2S,3S,4S)-4-methoxy-3-(4-methoxybenzyloxy)-2-methylhex-5-enal
  参考文献：
  名称：

  A convergent synthesis of the macrolide core of migrastatin

  摘要：

  We describe an efficient synthesis of the 14-membered macrolide core 2 of migrastatin via key intermediate 3 employing a diastereoselective aldol condensation, Lewis acid mediated diastereoselective addition and an exclusive (Z)-olefination sequence. Yamaguchi esterification of the key intermediate 3 followed by ring-closing metathesis (RCM) produced macrolide 2 with high selectivity and good yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.082

文献信息

• A Stereoselective Synthesis of the Macrolide Core of Migrastatin
  作者：Parthasarathi Das、Vobbalareddy Saibaba、Chetlur Kumar、Velisoju Mahendar

  DOI：10.1055/s-2008-1032028

  日期：2008.2

  A concise and efficient synthesis of the macrolide core of migrastatin, an antimetastatic agent, is reported. In this synthetic protocol, the key intermediate (4R,5S,6S)-6-methoxy-5-(4-meth­oxy­benzyloxy)-2,4-dimethylocta-2,7-dien-1-ol is obtained after dia­stereoselective aldol condensation, Lewis acid mediated diastereoselective addition, and an exclusive Z-olefination sequence have been employed. Yamaguchi esterification of the key intermediate, followed by ring-closing metathesis produced the desired macrolide in high selectivity and good yield.

  报道了一种针对迁移霉素（migrastatin）大环内酯核心的高效简洁合成方法。在该合成方案中，通过双键选择性aldol缩合、Lewis酸介导的手性选择性加成和专一的Z-型烯烃化反应序列，获得了关键中间体(4R,5S,6S)-6-甲氧基-5-(4-甲氧基苄氧基)-2,4-二甲基辛-2,7-二烯-1-醇。随后通过Yamaguchi酯化反应和环闭合复分解反应，高效且选择性良好地合成了目标大环内酯。
• A convergent synthesis of the macrolide core of migrastatin
  作者：V. Sai Baba、Parthasarathi Das、K. Mukkanti、Javed Iqbal

  DOI：10.1016/j.tetlet.2006.06.082

  日期：2006.8

  We describe an efficient synthesis of the 14-membered macrolide core 2 of migrastatin via key intermediate 3 employing a diastereoselective aldol condensation, Lewis acid mediated diastereoselective addition and an exclusive (Z)-olefination sequence. Yamaguchi esterification of the key intermediate 3 followed by ring-closing metathesis (RCM) produced macrolide 2 with high selectivity and good yield. (c) 2006 Elsevier Ltd. All rights reserved.