[(R)-deuterio-[(4R,5R)-4,5-dicyclohexyl-1,3,2-dioxaborolan-2-yl]-[dimethyl(phenyl)silyl]methyl] 2,2,6,6-tetramethylpiperidine-1-carboxylate | 1051943-06-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: [(R)-deuterio-[(4R,5R)-4,5-dicyclohexyl-1,3,2-dioxaborolan-2-yl]-[dimethyl(phenyl)silyl]methyl] 2,2,6,6-tetramethylpiperidine-1-carboxylate
• CAS: 1051943-06-6
• 化学式: C₃₃H₅₄BNO₄Si
• 分子量: 568.685
• InChiKey: NXSBTIHTEBJOAS-PKXBBOSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.66
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(R)-deuterio-[(4R,5R)-4,5-dicyclohexyl-1,3,2-dioxaborolan-2-yl]-[dimethyl(phenyl)silyl]methyl] 2,2,6,6-tetramethylpiperidine-1-carboxylate 在 三乙基硼氢化锂 作用下， 以 乙醚 为溶剂， 以79%的产率得到(R,R)-1,2-dicyclohexylethane-1,2-diol (1S)-(dimethylphenylsilyl)-[1-2H]methylboronate
  参考文献：
  名称：

  Formal and improved synthesis of enantiopure chiral methanol

  摘要：

  [D2]Methanol was converted to the carbamate derived from 2,2,6,6-tetramethylpiperidine. It was metalated with s-BuLi/TMEDA at -78 C with a high primary kinetic isotope effect to give an n.-oxymethyllithium, which was silylated with chlorodimethylphenylsilane. The silylmethyl carbamate formed was lithiated and borylated with the borate derived from tert-butanol and (R,R)-1,2-dicyclohexylethane-7,2-diol to give diastereomeric boronates, which were separated by preparative HPLC and can in principle be converted to enantiopure chiral methanols. Thus, both enantiomers are easily accessible in nine linear steps. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.091
• 作为产物：
  描述：

  (R,R)-1,2-dicyclohexylethane-1,2-diol tert-butyl alcohol borate 、 (dimethyl(phenyl)silyl)-[D₂]methyl 2,2,6,6-tetramethylpiperidine-1-carboxylate 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 乙醚 、 环己烷 为溶剂， 反应 2.0h， 以47%的产率得到[(R)-deuterio-[(4R,5R)-4,5-dicyclohexyl-1,3,2-dioxaborolan-2-yl]-[dimethyl(phenyl)silyl]methyl] 2,2,6,6-tetramethylpiperidine-1-carboxylate
  参考文献：
  名称：

  Formal and improved synthesis of enantiopure chiral methanol

  摘要：

  [D2]Methanol was converted to the carbamate derived from 2,2,6,6-tetramethylpiperidine. It was metalated with s-BuLi/TMEDA at -78 C with a high primary kinetic isotope effect to give an n.-oxymethyllithium, which was silylated with chlorodimethylphenylsilane. The silylmethyl carbamate formed was lithiated and borylated with the borate derived from tert-butanol and (R,R)-1,2-dicyclohexylethane-7,2-diol to give diastereomeric boronates, which were separated by preparative HPLC and can in principle be converted to enantiopure chiral methanols. Thus, both enantiomers are easily accessible in nine linear steps. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.091