Methyl (-)-6-<2-(tert-butyldiphenylsilyloxy)ethyl>-2-hydroxymethyl-3-(methoxymethoxy)piperidine-1-carboxylate | 144463-07-0

• 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: Methyl (-)-6-<2-(tert-butyldiphenylsilyloxy)ethyl>-2-hydroxymethyl-3-(methoxymethoxy)piperidine-1-carboxylate
• 英文别名: methyl (2R,3R,6R)-6-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-2-(hydroxymethyl)-3-(methoxymethoxy)piperidine-1-carboxylate
• CAS: 144463-07-0
• 化学式: C₂₈H₄₁NO₆Si
• 分子量: 515.722
• InChiKey: FAXADICBNPIAIP-DNRSQYFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl (-)-6-<2-(tert-butyldiphenylsilyloxy)ethyl>-2-hydroxymethyl-3-(methoxymethoxy)piperidine-1-carboxylate 在 palladium on activated charcoal 吡啶 、 盐酸 、 重铬酸吡啶 、 Raney Ni W-4 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 pyridinium chlorochromate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (2R,6R)-(-)-6-methyl-1-methoxycarbonylpiperidin-2-ylethanoate
  参考文献：
  名称：

  Asymmetric twin-ring differentiation by lipase-catalyzed enantiotoposelective reaction of the ring-crossed meso glycol: Asymmetric synthesis of a highly functionalized piperidine from the conjoined twin piperidine system

  摘要：

  Both enantiomers of the homochiral 3-oxygenated 2,6-cis-disubstituted piperidine 1 were synyhesized by starting with lipase-catalyzed transesterification or hydrolysis of the meso glycol or its diacetate in the conjoined twin piperidine system.

  DOI：

  10.1016/s0040-4039(00)79101-5
• 作为产物：
  描述：

  Dimethyl (+)-6-<2-(tert-butyldiphenylsilyloxy)ethyl>-3-(methoxymethoxy)piperidine-1,2-dicarboxylate 在 三乙基硼氢化锂 作用下， 以87%的产率得到Methyl (-)-6-<2-(tert-butyldiphenylsilyloxy)ethyl>-2-hydroxymethyl-3-(methoxymethoxy)piperidine-1-carboxylate
  参考文献：
  名称：

  Asymmetric twin-ring differentiation by lipase-catalyzed enantiotoposelective reaction of the ring-crossed meso glycol: Asymmetric synthesis of a highly functionalized piperidine from the conjoined twin piperidine system

  摘要：

  Both enantiomers of the homochiral 3-oxygenated 2,6-cis-disubstituted piperidine 1 were synyhesized by starting with lipase-catalyzed transesterification or hydrolysis of the meso glycol or its diacetate in the conjoined twin piperidine system.

  DOI：

  10.1016/s0040-4039(00)79101-5

文献信息

• Asymmetric twin-ring differentiation by lipase-catalyzed enantiotoposelective reaction of the ring-crossed meso glycol: Asymmetric synthesis of a highly functionalized piperidine from the conjoined twin piperidine system
  作者：Takefumi Momose、Naoki Toyooka、Makoto Jin

  DOI：10.1016/s0040-4039(00)79101-5

  日期：1992.9

  Both enantiomers of the homochiral 3-oxygenated 2,6-cis-disubstituted piperidine 1 were synyhesized by starting with lipase-catalyzed transesterification or hydrolysis of the meso glycol or its diacetate in the conjoined twin piperidine system.
• Asymmetric synthesis of the alkaloid 2,6-disubstituted piperidin-3-ols, (−)-cassine and (+)-spectaline
  作者：Takefumi Momose、Naoki Toyooka

  DOI：10.1016/s0040-4039(00)73860-3

  日期：1993.9

  The asymmetric total synthesis of (-)-cassine (1) and (+)-spectaline (2) was achieved by starting with both enantiomers of the homochiral 3-oxygenated 2,6-cis-disubstituted piperidine 3.
• Momose, Takefumi; Toyooka, Naoki; Jin, Makoto, Journal of the Chemical Society. Perkin transactions I, 1997, # 13, p. 2005 - 2013
  作者：Momose, Takefumi、Toyooka, Naoki、Jin, Makoto

  DOI：——

  日期：——