(3R,5S,6R)-1-(4-methoxybenzyloxy)-6-methyloct-7-ene-3,5-diol | 1018689-53-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R,5S,6R)-1-(4-methoxybenzyloxy)-6-methyloct-7-ene-3,5-diol
• 英文别名: (3R,5S,6R)-1-[(4-methoxyphenyl)methoxy]-6-methyloct-7-ene-3,5-diol
• CAS: 1018689-53-6
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: AJOIJQXEJWYNSL-UNEWFSDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,5S,6R)-1-(4-methoxybenzyloxy)-6-methyloct-7-ene-3,5-diol 在 咪唑 、 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (5S,7R)-5-((R)-but-3-en-2-yl)-9,9-diisopropyl-7-(2-(4-methoxybenzyloxy)ethyl)-10-methyl-2,4,8-trioxa-9-silaundecane
  参考文献：
  名称：

  Total Synthesis of Dolabelide C: A Phosphate-Mediated Approach

  摘要：

  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.

  DOI：

  10.1021/jo2003506
• 作为产物：
  描述：

  (4S,6R)-4-[(2R)-but-3-en-2-yl]-2-methoxy-6-[2-[(4-methoxyphenyl)methoxy]ethyl]-1,3,2lambda5-dioxaphosphinane 2-oxide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以96%的产率得到(3R,5S,6R)-1-(4-methoxybenzyloxy)-6-methyloct-7-ene-3,5-diol
  参考文献：
  名称：

  Total Synthesis of Dolabelide C: A Phosphate-Mediated Approach

  摘要：

  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.

  DOI：

  10.1021/jo2003506

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.