methyl (3S,4S,5S,6R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-4,6-dimethyl-7-oxoheptanoate | 1108178-11-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (3S,4S,5S,6R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-4,6-dimethyl-7-oxoheptanoate
• CAS: 1108178-11-5
• 化学式: C₂₂H₄₆O₅Si₂
• 分子量: 446.775
• InChiKey: IBSHFVAKRMKZNT-CGBFIWBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  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

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.