(2R,3S)-1-tert-butyloxycarbonyl-2-methoxycarbonyl-3-hydroxy-piperidine | 152230-79-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3S)-1-tert-butyloxycarbonyl-2-methoxycarbonyl-3-hydroxy-piperidine
• 英文别名: 1-(tert-Butyl) 2-methyl (2R,3S)-3-hydroxypiperidine-1,2-dicarboxylate；1-O-tert-butyl 2-O-methyl (2R,3S)-3-hydroxypiperidine-1,2-dicarboxylate
• CAS: 152230-79-0
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: DSCVRGCAXJUTEM-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-1-tert-butyloxycarbonyl-2-methoxycarbonyl-3-hydroxy-piperidine 在 盐酸 、 水 、 methyloxirane 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以99%的产率得到(2R,3S)-3-羟基-2-哌啶羧酸
  参考文献：
  名称：

  Facile Syntheses of Enantiopure 3-Hydroxypiperidine Derivatives and 3-Hydroxypipecolic Acids

  摘要：

  Facile syntheses of enantiopure trans- and cis-3-hydroxypiperidine derivatives and 3-hydroxypipecolic acids are reported, featuring Rh-catalyzed cyclohydrocarbonylation through common intermediates. A diaxial conformation in a 2,3-disubstituted N-Boc-piperidinyl structure is revealed by an X-ray crystallographic analysis.

  DOI：

  10.1021/jo902324h
• 作为产物：
  描述：

  (2R,3S)-1-tert-butyloxycarbonyl-2-methoxycarbonyl-3-benzyloxypiperidine 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、202.66 kPa 条件下， 反应 4.0h， 以84%的产率得到(2R,3S)-1-tert-butyloxycarbonyl-2-methoxycarbonyl-3-hydroxy-piperidine
  参考文献：
  名称：

  Facile Syntheses of Enantiopure 3-Hydroxypiperidine Derivatives and 3-Hydroxypipecolic Acids

  摘要：

  Facile syntheses of enantiopure trans- and cis-3-hydroxypiperidine derivatives and 3-hydroxypipecolic acids are reported, featuring Rh-catalyzed cyclohydrocarbonylation through common intermediates. A diaxial conformation in a 2,3-disubstituted N-Boc-piperidinyl structure is revealed by an X-ray crystallographic analysis.

  DOI：

  10.1021/jo902324h

文献信息

• Knight, David W.; Lewis, Neil; Share, Andrew C., Journal of the Chemical Society. Perkin transactions I, 1998, # 22, p. 3673 - 3683
  作者：Knight, David W.、Lewis, Neil、Share, Andrew C.、Haigh, David

  DOI：——

  日期：——
• New members of the chiral pool: β-Hydroxypiperidine carboxylates from Baker's yeast reductions of the corresponding keto-esters
  作者：David W. Knight、Neil Lewis、Andrew C. Share、David Haigh

  DOI：10.1016/s0957-4166(00)80164-0

  日期：1993.4

  Baker's yeast reduction of the keto-piperidinecarboxylates 2 and 6 leads to the corresponding hydroxy-esters 3 and 7a in good chemical yields and with >99% d.e. and >93% e.e. in both cases.
• Facile Syntheses of Enantiopure 3-Hydroxypiperidine Derivatives and 3-Hydroxypipecolic Acids
  作者：Wen-Hua Chiou、Gau-Hong Lin、Chih-Wei Liang

  DOI：10.1021/jo902324h

  日期：2010.3.5

  Facile syntheses of enantiopure trans- and cis-3-hydroxypiperidine derivatives and 3-hydroxypipecolic acids are reported, featuring Rh-catalyzed cyclohydrocarbonylation through common intermediates. A diaxial conformation in a 2,3-disubstituted N-Boc-piperidinyl structure is revealed by an X-ray crystallographic analysis.