(1R,6R,8R)-8-((3R,4S,5R,E)-6-((tert-butyldiphenylsilyl)oxy)-4-((4-methoxybenzyl)oxy)-3,5-dimethylhex-1-en-1-yl)-2,9,10-trioxa-1-phosphabicyclo[4.3.1]dec-4-ene 1-oxide | 1003890-54-7

• 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: (1R,6R,8R)-8-((3R,4S,5R,E)-6-((tert-butyldiphenylsilyl)oxy)-4-((4-methoxybenzyl)oxy)-3,5-dimethylhex-1-en-1-yl)-2,9,10-trioxa-1-phosphabicyclo[4.3.1]dec-4-ene 1-oxide
• CAS: 1003890-54-7
• 化学式: C₃₈H₄₉O₇PSi
• 分子量: 676.862
• InChiKey: HDDAAJXHUWAYDN-DTZNVXLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.85
• 重原子数：
  47.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 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 、 tert-butyl(((2R,3S,4R)-3-((4-methoxybenzyl)oxy)-2,4-dimethylhex-5-en-1-yl)oxy)diphenylsilane 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 甲苯 为溶剂， 以31%的产率得到(1R,6R,8R)-8-((3R,4S,5R,E)-6-((tert-butyldiphenylsilyl)oxy)-4-((4-methoxybenzyl)oxy)-3,5-dimethylhex-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