(6R)-6-[tert-butyl(dimethyl)silyl]oxy-6-[(2S,3R)-3-methyloxiran-2-yl]hexan-2-one | 1242647-75-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6R)-6-[tert-butyl(dimethyl)silyl]oxy-6-[(2S,3R)-3-methyloxiran-2-yl]hexan-2-one
• CAS: 1242647-75-1
• 化学式: C₁₅H₃₀O₃Si
• 分子量: 286.487
• InChiKey: JGCBHIZCZSWRFZ-MCIONIFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6R)-6-[tert-butyl(dimethyl)silyl]oxy-6-[(2S,3R)-3-methyloxiran-2-yl]hexan-2-one 在 四丁基氟化铵 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以92%的产率得到(6R)-6-hydroxy-6-[(2R,3R)-3-methyloxiran-2-yl]hexan-2-one
  参考文献：
  名称：

  Highly α-Selective Hydrolysis of α,β-Epoxyalcohols using Tetrabutylammonium Fluoride

  摘要：

  We report a simple method for the highly regio- and stereoselective hydrolysis of alpha,beta-epoxyalcohols. Treatment of enantiopure epoxyalcohols derived from Sharpless epoxidation with TBAF/H(2)O resulted in exclusive ring opening at the normally disfavored alpha-position, providing access to arabino- or lyxo-configured triols with full preservation of stereochemical purity. The method was applied in syntheses of 5-deoxy-L-arabinose (26) and a family of bicyclic acetals based on the insect pheromone hydroxybrevicomin (4).

  DOI：

  10.1021/ol1015306
• 作为产物：
  描述：

  在 水 、 copper(l) chloride 、 palladium dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以75%的产率得到(6R)-6-[tert-butyl(dimethyl)silyl]oxy-6-[(2S,3R)-3-methyloxiran-2-yl]hexan-2-one
  参考文献：
  名称：

  Highly α-Selective Hydrolysis of α,β-Epoxyalcohols using Tetrabutylammonium Fluoride

  摘要：

  We report a simple method for the highly regio- and stereoselective hydrolysis of alpha,beta-epoxyalcohols. Treatment of enantiopure epoxyalcohols derived from Sharpless epoxidation with TBAF/H(2)O resulted in exclusive ring opening at the normally disfavored alpha-position, providing access to arabino- or lyxo-configured triols with full preservation of stereochemical purity. The method was applied in syntheses of 5-deoxy-L-arabinose (26) and a family of bicyclic acetals based on the insect pheromone hydroxybrevicomin (4).

  DOI：

  10.1021/ol1015306