(R,E)-1-iodo-4-(methoxymethoxy)-2-methylhept-1-ene | 1018689-59-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R,E)-1-iodo-4-(methoxymethoxy)-2-methylhept-1-ene
• 英文别名: (1E,4R)-1-iodo-4-methoxymethoxy-2-methylhept-1-ene；(E,4R)-1-iodo-4-(methoxymethoxy)-2-methylhept-1-ene
• CAS: 1018689-59-2
• 化学式: C₁₀H₁₉IO₂
• 分子量: 298.164
• InChiKey: JGHQUOJFRKNJFW-TTZKWOQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R,E)-1-iodo-4-(methoxymethoxy)-2-methylhept-1-ene 、 (2S,3S,5R)-3-(tert-Butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-5-(4-methoxybenzyloxy)-2-methylnonanal 在 叔丁基锂 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 (4R,6E,8R,9R,10S,12R)-10-(tert-butyldimethylsiloxy)-16-(tert-butyldiphenylsiloxy)-12-(4-methoxybenzyloxy)-4-methoxymethoxy-6,9-dimethylhexadec-6-en-8-ol 、
  参考文献：
  名称：

  Ruthenium-SYNPHOS-Catalyzed Asymmetric Hydrogenations: an Entry to Highly Stereoselective Synthesis of the C15−C30 Subunit of Dolabelide A

  摘要：

  An efficient construction of the C15-C30 segment of the cytotoxic macrolide dolabelide A is described. The synthesis relies on ruthenium-SYNPHOS-mediated asymmetric hydrogenation reactions of beta-keto esters to generate the C19, C21, and C27 hydroxyl-bearing stereocenters with very high levels of enantio- and diastereoselectivity.

  DOI：

  10.1021/ol801493w
• 作为产物：
  描述：

  (1E,4R)-1-iodo-2-methylhept-1-en-4-ol 、 氯甲基甲基醚 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到(R,E)-1-iodo-4-(methoxymethoxy)-2-methylhept-1-ene
  参考文献：
  名称：

  Ruthenium-SYNPHOS-Catalyzed Asymmetric Hydrogenations: an Entry to Highly Stereoselective Synthesis of the C15−C30 Subunit of Dolabelide A

  摘要：

  An efficient construction of the C15-C30 segment of the cytotoxic macrolide dolabelide A is described. The synthesis relies on ruthenium-SYNPHOS-mediated asymmetric hydrogenation reactions of beta-keto esters to generate the C19, C21, and C27 hydroxyl-bearing stereocenters with very high levels of enantio- and diastereoselectivity.

  DOI：

  10.1021/ol801493w

文献信息

• A Multifaceted Phosphate Tether:  Application to the C15−C30 Subunit of Dolabelides A−D
  作者：Alan Whitehead、Joshua D. Waetzig、Christopher D. Thomas、Paul R. Hanson

  DOI：10.1021/ol8001865

  日期：2008.4.1

  Construction of the C15-C30 subunit of dolabelide utilizing a temporary phosphate tether is described. Two routes are reported that make use of the orthogonal protecting- and leaving-group properties innate to phosphate esters. One route relies on a selective terminal oxidation, while a second utilizes a CM/selective hydrogenation sequence. Both routes depend on a highly regio- and diastereoselective cuprate addition to set the requisite stereochemistry at C22.
• Total Synthesis of Dolabelide C: A Phosphate-Mediated Approach
  作者：Paul R. Hanson、Rambabu Chegondi、John Nguyen、Christopher D. Thomas、Joshua D. Waetzig、Alan Whitehead

  DOI：10.1021/jo2003506

  日期：2011.6.3

  The first synthesis of dolabelide C (1), a cytotoxic marine macrolide, is reported utilizing a phosphate tether-mediated approach. Bicyclic phosphates (S,S,S-p)-5 and (R,R,R-p)-5 serve as the central building blocks for the construction of two major 1,3-anti-diol subunits in 1 through selective cleavage pathways, regioselective olefin reduction, and cross-metathesis. Overall, phosphate-mediated processes provided copious amounts of both major subunits allowing for a detailed RCM macrocyclization study to the 24-membered macrolactone 1.