(2S*,3S*)-4-(tert-butyldimethylsiloxy)-2-ethyl-1,3-butanediol

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S*,3S*)-4-(tert-butyldimethylsiloxy)-2-ethyl-1,3-butanediol
• 英文别名: (2R,3R)-4-[tert-butyl(dimethyl)silyl]oxy-2-ethylbutane-1,3-diol
• 化学式: C₁₂H₂₈O₃Si
• 分子量: 248.438
• InChiKey: BXUQGEZUGPBNRV-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三乙基铝 、 ((2S,3S)-3-(((tert-butyldimethylsilyl)oxy)methyl)oxiran-2-yl)methanol 在 正丁基锂 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (2S,3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]pentane-1,2-diol 、 (2S*,3S*)-4-(tert-butyldimethylsiloxy)-2-ethyl-1,3-butanediol
  参考文献：
  名称：

  Regioselective Alkyl and Alkynyl Substitution Reactions of Epoxy Alcohols by the Use of Organoaluminum Ate Complexes:  Regiochemical Reversal of Nucleophilic Substitution Reactions

  摘要：

  Unprecedented nucleophilic substitution reactions of 2,3-epoxy-1-alkanols with alkyl and alkynylaluminum ate complexes have been studied and demonstrated to occur at the C2 position with extremely high stereoselectivity, i.e., with exactly reversed regioselectivity to that obtained in the substitution reactions by normal organoaluminum reagents, resulting in the formation of the C2-alkyl and C2-alkynyl substitution products in excellent yields.

  DOI：

  10.1021/ol010062+

文献信息

• Regioselective Alkyl and Alkynyl Substitution Reactions of Epoxy Alcohols by the Use of Organoaluminum Ate Complexes:  Regiochemical Reversal of Nucleophilic Substitution Reactions
  作者：Minoru Sasaki、Keiji Tanino、Masaaki Miyashita

  DOI：10.1021/ol010062+

  日期：2001.5.1

  Unprecedented nucleophilic substitution reactions of 2,3-epoxy-1-alkanols with alkyl and alkynylaluminum ate complexes have been studied and demonstrated to occur at the C2 position with extremely high stereoselectivity, i.e., with exactly reversed regioselectivity to that obtained in the substitution reactions by normal organoaluminum reagents, resulting in the formation of the C2-alkyl and C2-alkynyl substitution products in excellent yields.