[(2R,3S,5R,7S)-7-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-4-methylidene-1-oxaspiro[2.5]octan-2-yl]methyl acetate | 138381-67-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,5R,7S)-7-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-4-methylidene-1-oxaspiro[2.5]octan-2-yl]methyl acetate
• CAS: 138381-67-6
• 化学式: C₁₇H₃₀O₅Si
• 分子量: 342.508
• InChiKey: GGDIGAGCKSWGGD-HWMZRRJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  68.29
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R,7S)-7-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-4-methylidene-1-oxaspiro[2.5]octan-2-yl]methyl acetate 在 dirhodium tetraacetate 2-叠氮丙二酸二甲酯 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 生成 Acetic acid 2-[(3S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-3-fluoro-2-methylene-cyclohex-(Z)-ylidene]-ethyl ester
  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
• 作为产物：
  描述：

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