[(2S,3R,5S,7S)-7-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-4-methylidene-1-oxaspiro[2.5]octan-2-yl]methyl acetate | 138307-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,5S,7S)-7-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-4-methylidene-1-oxaspiro[2.5]octan-2-yl]methyl acetate
• CAS: 138307-75-2
• 化学式: C₁₇H₃₀O₅Si
• 分子量: 342.508
• InChiKey: GGDIGAGCKSWGGD-QBYUYEEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  [(2S,3R,7S)-7-[tert-butyl(dimethyl)silyl]oxy-4-methylidene-1-oxaspiro[2.5]octan-2-yl]methyl acetate 在 吡啶-N-氧化物 、 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 以69%的产率得到[(2S,3R,5S,7S)-7-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-4-methylidene-1-oxaspiro[2.5]octan-2-yl]methyl acetate
  参考文献：
  名称：

  Chemical conversion of vitamin D3 to its 1,35-dihydroxy metabolite

  摘要：

  Vitamin D3 (6) has been converted to the 1,25-dihydroxy vitamin D3 metabolite (1) and the 1-alpha-fluoro derivative 2 via a new process. The strategy involved the cleavage of the ring A portion from the CD portion in vitamin D3 followed by the individual modification of each subunit ot form 3, 4, and 5. The subsequent recombination of 3 and 5 formed 1 while 4 and 5 produced 2.

  DOI：

  10.1016/0040-4039(91)80752-r