(1S,6S,8R)-8-(2-((4-methoxybenzyl)oxy)ethyl)-2,9,10-trioxa-1-phosphabicyclo[4.3.1]dec-4-ene 1-oxide | 1018689-49-0

• 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: (1S,6S,8R)-8-(2-((4-methoxybenzyl)oxy)ethyl)-2,9,10-trioxa-1-phosphabicyclo[4.3.1]dec-4-ene 1-oxide
• CAS: 1018689-49-0
• 化学式: C₁₆H₂₁O₆P
• 分子量: 340.313
• InChiKey: FJBHSZUJXIJBQE-CKNGIIGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1S,6S,8R)-8-(2-((4-methoxybenzyl)oxy)ethyl)-2,9,10-trioxa-1-phosphabicyclo[4.3.1]dec-4-ene 1-oxide 、 Dimethylzinc 、 三甲基硅烷化重氮甲烷 在 copper(I) cyanide di(lithium chloride) 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以87%的产率得到(4S,6R)-4-[(2R)-but-3-en-2-yl]-2-methoxy-6-[2-[(4-methoxyphenyl)methoxy]ethyl]-1,3,2lambda5-dioxaphosphinane 2-oxide
  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,6S)-4,6-diethenyl-2-(2-propen-1-yloxy)-1,3,2-dioxaphosphorinane 2-oxide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-甲基苯磺酸吡啶 、 9-硼双环[3.3.1]壬烷 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,6S,8R)-8-(2-((4-methoxybenzyl)oxy)ethyl)-2,9,10-trioxa-1-phosphabicyclo[4.3.1]dec-4-ene 1-oxide
  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