(2R,3S)-tert-butyl 2-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)piperidine-1-carboxylate | 1174386-88-9

• 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: (2R,3S)-tert-butyl 2-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)piperidine-1-carboxylate
• 英文别名: tert-butyl (2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-(phenylmethoxymethyl)piperidine-1-carboxylate
• CAS: 1174386-88-9
• 化学式: C₂₄H₄₁NO₄Si
• 分子量: 435.679
• InChiKey: QDVPIEWDBGPDFE-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.99
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (2R,3S)-tert-butyl 2-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)piperidine-1-carboxylate 在 sodium periodate 、 ruthenium(III) chloride trihydrate 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 24.5h， 生成 (2S,3S)-1-(tert-butoxycarbonyl)-3-((tert-butyldimethylsilyl)oxy)piperidine-2-carboxylic acid
  参考文献：
  名称：

  Concise Enantioselective Syntheses of (+)-L-733,060 and (2S,3S)-3-Hydroxypipecolic Acid by Cobalt(III)(salen)-Catalyzed Two-Stereocenter Hydrolytic Kinetic Resolution of Racemic Azido Epoxides

  摘要：

  An efficient synthesis of the 2,3-disubstituted piperidines (+)-L-733,060 and (2S,3S)-3-hydroxypipecolic acid (99% ee) in high optical purity from commercially available starting materials is described. The strategy involves a cobalt-catalyzed hydrolytic kinetic resolution of a racemic azido epoxide with two stereocenters and an intramolecular reductive cyclization as key reactions.

  DOI：

  10.1055/s-0033-1340074
• 作为产物：
  描述：

  (5S,6R)-5-<(tert-Butyldimethylsilyl)oxy>-6-<(benzyloxy)methyl>-2-piperidinone 在 dimethyl sulfide borane 、 sodium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 (2R,3S)-tert-butyl 2-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)piperidine-1-carboxylate
  参考文献：
  名称：

  Concise Enantioselective Syntheses of (+)-L-733,060 and (2S,3S)-3-Hydroxypipecolic Acid by Cobalt(III)(salen)-Catalyzed Two-Stereocenter Hydrolytic Kinetic Resolution of Racemic Azido Epoxides

  摘要：

  An efficient synthesis of the 2,3-disubstituted piperidines (+)-L-733,060 and (2S,3S)-3-hydroxypipecolic acid (99% ee) in high optical purity from commercially available starting materials is described. The strategy involves a cobalt-catalyzed hydrolytic kinetic resolution of a racemic azido epoxide with two stereocenters and an intramolecular reductive cyclization as key reactions.

  DOI：

  10.1055/s-0033-1340074

文献信息

• Stereospecific, Flexible and Redox-Economic Asymmetric Synthesis of<i>cis</i>- and<i>trans</i>-3-Hydroxypipecolic Acids and ­Analogs
  作者：Bing Wang、Run-Hua Liu

  DOI：10.1002/ejoc.200900231

  日期：2009.6

  trans-3-hydroxy-L-pipecolic acids are synthesized from a common chiral intermediate 7 by a short and flexible route. The stereospecific inversion of C-3 was achieved by the formation of an oxazoline followed by acidic ring cleavage. The overall yields are 27 % and 30 %, respectively, in 12 and 10 linear steps. Several versatile chiral building blocks are also accessible by this diastereodivergent synthesis. Unlike the

  顺式和反式 3-羟基-L-哌啶酸均由常见的手性中间体 7 通过短而灵活的途径合成。C-3 的立体有择反转是通过形成恶唑啉，然后进行酸性环裂解来实现的。在 12 和 10 个线性步骤中，总产率分别为 27% 和 30%。这种非对映发散合成也可以使用几种通用的手性构件。与手性池方法不同，我们的合成策略不受起始材料可用性的限制。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Asymmetric total synthesis of (2S,3S)-3-hydroxypipecolic acid
  作者：Subhash P. Chavan、Nilesh B. Dumare、Kishor R. Harale、Uttam R. Kalkote

  DOI：10.1016/j.tetlet.2010.11.062

  日期：2011.1

  A synthetic route to (2S,3S)-3-hydroxypipecolic acid was achieved from readily available nonchiral pool starting material cis-2-butene-1,4-diol and involved Claisen orthoester rearrangement, Sharpless asymmetric dihydroxylation and intramolecular lactamisation of azido lactone as the key steps. (C) 2010 Elsevier Ltd. All rights reserved.
• Concise Enantioselective Syntheses of (+)-L-733,060 and (2S,3S)-3-Hydroxypipecolic Acid by Cobalt(III)(salen)-Catalyzed Two-Stereocenter Hydrolytic Kinetic Resolution of Racemic Azido Epoxides
  作者：Arumugam Sudalai、Dattatray Devalankar、Pandurang Chouthaiwale

  DOI：10.1055/s-0033-1340074

  日期：——

  An efficient synthesis of the 2,3-disubstituted piperidines (+)-L-733,060 and (2S,3S)-3-hydroxypipecolic acid (99% ee) in high optical purity from commercially available starting materials is described. The strategy involves a cobalt-catalyzed hydrolytic kinetic resolution of a racemic azido epoxide with two stereocenters and an intramolecular reductive cyclization as key reactions.