(3R,4S,6R)-8-(4-methoxybenzyloxy)-3-methyl-6-(triisopropylsilyloxy)oct-1-en-4-ol | 1018689-73-0

• 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: (3R,4S,6R)-8-(4-methoxybenzyloxy)-3-methyl-6-(triisopropylsilyloxy)oct-1-en-4-ol
• 英文别名: (3R,4S,6R)-8-[(4-methoxyphenyl)methoxy]-3-methyl-6-tri(propan-2-yl)silyloxyoct-1-en-4-ol
• CAS: 1018689-73-0
• 化学式: C₂₆H₄₆O₄Si
• 分子量: 450.734
• InChiKey: XNOXTJXHDPLPMC-RCXJIHSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.74
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S,6R)-8-(4-methoxybenzyloxy)-3-methyl-6-(triisopropylsilyloxy)oct-1-en-4-ol 在 吡啶 、 三乙烯二胺 、 叔丁基锂 、 臭氧 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 zinc dibromide 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 [(E,3R,5S,6S,7R,11R)-5,7,11-tris(methoxymethoxy)-6,9-dimethyl-3-tri(propan-2-yl)silyloxytetradec-8-enyl] 4-methylbenzenesulfonate
  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 咪唑 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (3R,4S,6R)-8-(4-methoxybenzyloxy)-3-methyl-6-(triisopropylsilyloxy)oct-1-en-4-ol
  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.