tert-butyl (2R,3S)-3-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)piperidine-1-carboxylate | 1174386-89-0

• 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: tert-butyl (2R,3S)-3-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)piperidine-1-carboxylate
• 英文别名: 1-Piperidinecarboxylic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-, 1,1-dimethylethyl ester, (2R,3S)-；tert-butyl (2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)piperidine-1-carboxylate
• CAS: 1174386-89-0
• 化学式: C₁₇H₃₅NO₄Si
• 分子量: 345.555
• InChiKey: IPGSAOQJRLRTNS-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 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 (2R,3S)-3-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)piperidine-1-carboxylate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以96%的产率得到(2R,3S)-2-hydroxymethylpiperidin-3-ol
  参考文献：
  名称：

  顺式和反式 3-羟基哌啶酸和类似物的立体有择、灵活和氧化还原经济不对称合成

  摘要：

  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)

  DOI：

  10.1002/ejoc.200900231
• 作为产物：
  描述：

  (5S,6R)-5-<(tert-Butyldimethylsilyl)oxy>-6-<(benzyloxy)methyl>-2-piperidinone 在 dimethyl sulfide borane 、 palladium 10% on activated carbon 、 氢气 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 42.0h， 生成 tert-butyl (2R,3S)-3-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)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

• [EN] NOVEL HETEROCYCLIC COMPOUND, ITS PREPARATION METHOD, AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME<br/>[FR] NOUVEAU COMPOSÉ HÉTÉROCYCLIQUE, SON PROCÉDÉ DE PRÉPARATION ET COMPOSITION PHARMACEUTIQUE LE COMPRENANT
  申请人：DAE WOONG PHARMA

  公开号：WO2018147626A1

  公开（公告）日：2018-08-16

  The present invention relates to a heterocyclic compound represented by Chemical Formula 1 that can be used for the prevention or treatment of diseases caused by abnormality in a PRS (prolyl-tRNA synthetase) activity, or a pharmaceutically acceptable salt thereof, a method for preparing the same, and a pharmaceutical composition comprising the same.

  本发明涉及一种由化学式1表示的杂环化合物，可用于预防或治疗由PRS（脯氨酰-tRNA合成酶）活性异常引起的疾病，或其药用可接受的盐，以及制备该化合物的方法和包含该化合物的药物组合物。
• 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.
• [EN] FUSED RING KRAS INHIBITORS FOR TREATING DISEASE<br/>[FR] INHIBITEURS DE KRAS À CYCLES FUSIONNÉS POUR LE TRAITEMENT D'UNE MALADIE
  申请人：[en]BLOSSOMHILL THERAPEUTICS, INC.

  公开号：WO2024015262A1

  公开（公告）日：2024-01-18

  The present disclosure relates to fused ring compounds targeting KRAS, pharmaceutical compositions containing the compounds, and methods of using such compounds to treat disease, such as cancer.
• [EN] METHOD FOR PREPARATION OF (2R, 3S)-2-(BENZO[D]IMIDAZOLYLPROPYL)PIPERIDIN-3-OL DERIVATIVES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DÉRIVÉS DE (2R,3S)-2-(BENZO[D]IMIDAZOLYLPROPYL)PIPÉRIDIN-3-OL<br/>[KO] (2R, 3S)-2-(벤조[D]이미다졸일프로필)피페리딘-3-올 유도체의 제조 방법
  申请人：[en]DAEWOONG PHARMACEUTICAL CO., LTD.;[ko]주식회사 대웅제약

  公开号：WO2023113534A1

  公开（公告）日：2023-06-22

  본 발명은 (2R, 3S)-2-(벤조[d]이미다졸일프로필)피페리딘-3-올 유도체의 제조 방법에 관한 것으로, 본 발명에 따른 제조 방법은, 단축된 공정으로도 상기 화합물을 높은 수율로 제조할 수 있다는 이점이 있다.
• 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.