tert-butyl (2S,3S)-3-(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate | 1171122-40-9

• 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: tert-butyl (2S,3S)-3-(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate
• 英文别名: (2S,3S)-1-tert-butyloxycarbonyl-2-hydroxymethyl-3-benzyloxypiperidine；tert-butyl (2S,3S)-2-(hydroxymethyl)-3-phenylmethoxypiperidine-1-carboxylate
• CAS: 1171122-40-9
• 化学式: C₁₈H₂₇NO₄
• 分子量: 321.417
• InChiKey: ICFRCLARUNRDBE-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3S)-3-(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以95%的产率得到(2S,3S)-tert-butyl 3-hydroxy-2-(hydroxymethyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Chiron approach to formal synthesis of both antipodes of cis 3-hydroxypipecolic acid

  摘要：

  The efficient and practical formal syntheses of both enantiomers of cis 3-hydroxypipecolic acid were accomplished from cis aziridine-2-carboxylate as the common synthetic precursor. The key steps involved are stereo and regioselective aziridine ring opening, reductive cyclization and selective N-debenzylation over O-debenzylation reactions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.118
• 作为产物：
  描述：

  (1S,2S,6R)-2-benzyloxy-8-tert-butyloxycarbonyl-6-oxa-8-azabicyclo[3.2.1]octane 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以213 mg的产率得到tert-butyl (2S,3S)-3-(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate
  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

• A regioselective reductive cleavage of benzylidene acetal: stereoselective synthesis of N-Boc-protected cis-(2R,3S)-3-hydroxy pipecolic acid
  作者：Ponminor Senthil Kumar、Sundarababu Baskaran

  DOI：10.1016/j.tetlet.2009.03.007

  日期：2009.7

  A stereoselective synthesis of N-Boc-protected cis-(2R,3S)-3-hydroxy pipecolic acid, starting from d-glucose is described. The key step in the overall synthesis is a highly regioselective reductive cleavage of benzylidene acetal 13 leading to hydroxymethyl piperidine derivative 14.

  描述了从d-葡萄糖开始的N -Boc保护的顺式-（2 R，3 S）-3-羟基胡椒酸的立体选择性合成。整个合成过程中的关键步骤是亚苄基乙缩醛13的高度区域选择性还原性裂解，生成羟甲基哌啶衍生物14。
• 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.
• Chiron approach to formal synthesis of both antipodes of cis 3-hydroxypipecolic acid
  作者：Subhash P. Chavan、Lalit B. Khairnar、Prakash N. Chavan、Nilesh B. Dumare、Dinesh B. Kalbhor、Rajesh G. Gonnade

  DOI：10.1016/j.tetlet.2014.09.118

  日期：2014.11

  The efficient and practical formal syntheses of both enantiomers of cis 3-hydroxypipecolic acid were accomplished from cis aziridine-2-carboxylate as the common synthetic precursor. The key steps involved are stereo and regioselective aziridine ring opening, reductive cyclization and selective N-debenzylation over O-debenzylation reactions. (C) 2014 Elsevier Ltd. All rights reserved.