(1R,6R,8R)-8-((3R,E)-3-((4S,5R)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)but-1-en-1-yl)-2,9,10-trioxa-1-phosphabicyclo[4.3.1]dec-4-ene 1-oxide | 1003890-56-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1R,6R,8R)-8-((3R,E)-3-((4S,5R)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)but-1-en-1-yl)-2,9,10-trioxa-1-phosphabicyclo[4.3.1]dec-4-ene 1-oxide
• CAS: 1003890-56-9
• 化学式: C₂₂H₂₉O₇P
• 分子量: 436.442
• InChiKey: DQCWIGVHKLLICL-JGZHEMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  (1S,6R,8R)-8-Vinyl-2,9,10-trioxa-1-phospha-bicyclo[4.3.1]dec-4-ene 1-oxide 、 (4S,5R)-2-(4-Methoxy-phenyl)-5-methyl-4-((R)-1-methyl-allyl)-[1,3]dioxane 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 1,2-二氯乙烷 为溶剂， 以73%的产率得到(1R,6R,8R)-8-((3R,E)-3-((4S,5R)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)but-1-en-1-yl)-2,9,10-trioxa-1-phosphabicyclo[4.3.1]dec-4-ene 1-oxide
  参考文献：
  名称：

  A Multifaceted Phosphate Tether:  Application to the C1−C14 Subunit of Dolabelides A−D

  摘要：

  A phosphate tether approach to the C1-14 subunit of dolabelide is described. The phosphate tether serves a multifaceted role mediating several processes, including (i) diastereotopic differentiation via RCM, (ii) selective CM by imparting Type III behavior to the exocyclic olefin, (iii) regioselective hydrogenation, and (iv) regioselective Pd(0)-catalyzed reductive opening of the bicyclic phosphate. Overall, this strategy uses orthogonal protecting- and leaving-group properties innate to phosphate esters to rapidly assembly the titled subunit.

  DOI：

  10.1021/ol7025944