tert-butyl-[(1R,2S,6S,7S)-6-[tert-butyl(dimethyl)silyl]oxy-4-[diethoxy(oxido)phosphaniumyl]-2,7-dimethylcyclohept-3-en-1-yl]oxy-dimethylsilane | 1108178-07-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: tert-butyl-[(1R,2S,6S,7S)-6-[tert-butyl(dimethyl)silyl]oxy-4-[diethoxy(oxido)phosphaniumyl]-2,7-dimethylcyclohept-3-en-1-yl]oxy-dimethylsilane
• CAS: 1108178-07-9
• 化学式: C₂₅H₅₃O₅PSi₂
• 分子量: 520.838
• InChiKey: NHXDOWMQVPSJSB-BAMDZGJYSA-N

物化性质

• 沸点：
  493.4±45.0 °C(predicted)
• 密度：
  0.97±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.52
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  60
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 tert-butyl-[(1R,2S,6S,7S)-6-[tert-butyl(dimethyl)silyl]oxy-4-[diethoxy(oxido)phosphaniumyl]-2,7-dimethylcyclohept-3-en-1-yl]oxy-dimethylsilane 在 碳酸氢钠 、 臭氧 、 二甲基硫 作用下， 以 乙酸乙酯 为溶剂， 以81%的产率得到methyl (3S,4S,5S,6R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-4,6-dimethyl-7-oxoheptanoate
  参考文献：
  名称：

  Designer Discodermolide Segments via Ozonolysis of Vinyl Phosphonates

  摘要：

  To apply our collection of enantiopure 7-ring vinyl sulfones to probe the anticancer SAR of a series of computer-designed (+)-discodermolide analogs, the ozonolytic reactivity of transposed cyclic vinyl phosphonates was explored. Successful preparation of the desired aldehyde-esters and lactones from vinyl phosphonates via an oxidative cleavage-phosphite/methanol exchange sequence is described.

  DOI：

  10.1021/ol802503h
• 作为产物：
  描述：

  (((1S,2S,3S,4R)-2,4-dimethyl-5-(phenylsulfonyl)cyclohept-5-ene-1,3-diyl)bis(oxy))bis(tert-butyldimethylsilane) 、 亚磷酸二乙酯 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以962 mg的产率得到tert-butyl-[(1R,2S,6S,7S)-6-[tert-butyl(dimethyl)silyl]oxy-4-[diethoxy(oxido)phosphaniumyl]-2,7-dimethylcyclohept-3-en-1-yl]oxy-dimethylsilane
  参考文献：
  名称：

  Designer Discodermolide Segments via Ozonolysis of Vinyl Phosphonates

  摘要：

  To apply our collection of enantiopure 7-ring vinyl sulfones to probe the anticancer SAR of a series of computer-designed (+)-discodermolide analogs, the ozonolytic reactivity of transposed cyclic vinyl phosphonates was explored. Successful preparation of the desired aldehyde-esters and lactones from vinyl phosphonates via an oxidative cleavage-phosphite/methanol exchange sequence is described.

  DOI：

  10.1021/ol802503h

文献信息

• Designer Discodermolide Segments via Ozonolysis of Vinyl Phosphonates
  作者：Xavier Mollat du Jourdin、Mohammad Noshi、P. L. Fuchs

  DOI：10.1021/ol802503h

  日期：2009.2.5

  To apply our collection of enantiopure 7-ring vinyl sulfones to probe the anticancer SAR of a series of computer-designed (+)-discodermolide analogs, the ozonolytic reactivity of transposed cyclic vinyl phosphonates was explored. Successful preparation of the desired aldehyde-esters and lactones from vinyl phosphonates via an oxidative cleavage-phosphite/methanol exchange sequence is described.