methyl (5R,6R)-5-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-6-methylheptanoate | 1108178-08-0

• 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 (5R,6R)-5-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-6-methylheptanoate
• CAS: 1108178-08-0
• 化学式: C₁₅H₃₂O₄Si
• 分子量: 304.502
• InChiKey: SRUWIRTYJKCFTP-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲醇 、 tert-butyl-[(1R,2R)-4-[diethoxy(oxido)phosphaniumyl]-2-methylcyclohept-3-en-1-yl]oxy-dimethylsilane 在 吡啶 、 臭氧 、 4-二甲氨基吡啶 、 三溴化硼 、 叔丁胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以82%的产率得到methyl (5R,6R)-5-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-6-methylheptanoate
  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.