tert-butyl (2S,3S)-3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate | 130193-01-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (2S,3S)-3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate
• 英文别名: (2S,3S)-tert-Butyl 3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate
• CAS: 130193-01-0
• 化学式: C₁₀H₁₉NO₄
• 分子量: 217.265
• InChiKey: GIIDZEBNRLNGMS-YUMQZZPRSA-N

物化性质

• 沸点：
  340.3±27.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3S)-3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate 在 重铬酸吡啶 、 甲酸 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.34h， 生成 (2R,3S)-3-Benzyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
  参考文献：
  名称：

  Conformational Studies of Peptides Containing cis-3-Hydroxy-d-proline

  摘要：

  Conformational analysis of peptides containing cis-3-hydroxy-D-proline (D-cis-3-Hyp) by NMR studies revealed that the 3-hydroxyl group in this amino acid plays a significant role in the overall three-dimensional structures of the peptides. When the D-cis-3-Hyp had its 3-hydroxyl group protected as the benzyl (Bn) ether, the peptide displayed a beta-hairpin structure in both CDCl3 and DMSO-d(6). Even after the removal of the Bn group, the resulting deprotected compound retained the same structure as in the protected version in CDCl3. However, in polar solvent DMSO-d(6), the C-terminal strand of the hydroxyl-deprotected peptide flipped to the side of the hydroxyl group, breaking the hairpin to form a pseudo beta-turn-like nine-membered ring structure involving an intramolecular hydrogen bond between LeuNH --> HypC3-OH.

  DOI：

  10.1021/jo048893r
• 作为产物：
  描述：

  1-(tert-butyl) 2-methyl (2R,3S)-3-hydroxypyrrolidine-1,2-dicarboxylate 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 以793 mg的产率得到tert-butyl (2S,3S)-3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  [EN] SULFONAMIDE COMPOUNDS HAVING TNAP INHIBITORY ACTIVITY
  [FR] COMPOSÉS DE SULFONAMIDE AYANT UNE ACTIVITÉ INHIBITRICE DE TNAP

  摘要：

  本发明涉及一种具有优异的组织非特异性碱性磷酸酶抑制活性的化合物或其药理学上可接受的盐。本发明提供一种由式(I)表示的化合物或其药理学上可接受的盐。

  公开号：

  WO2018119444A1

文献信息

• 7-SUBSTITUTED 1-ARYL-NAPHTHYRIDINE-3-CARBOXYLIC ACID AMIDES AND USE THEREOF
  申请人：Bayer Aktiengesellschaft

  公开号：US20190263805A1

  公开（公告）日：2019-08-29

  The present application relates to novel 7-substituted 1-arylnaphthyridine-3-carboxamides, to processes for their preparation, to their use, alone or in combinations, for the treatment and/or prevention of diseases, and to their use for the production of medicaments for the treatment and/or prevention of diseases, in particular for the treatment and/or prevention of cardiovascular disorders and/or renal disorders.

  本申请涉及新颖的7-取代的1-芳基喹啉并吡啶-3-羧酰胺，其制备方法，其单独或组合使用，用于治疗和/或预防疾病，以及用于生产药物以治疗和/或预防疾病，特别是用于治疗和/或预防心血管疾病和/或肾脏疾病。
• Preparation of Chiral Contiguous Epoxyaziridines and Their Regioselective Ring-Opening for Drug Syntheses
  作者：Hui Mao、Hyeonsu Jeong、Jieun Yang、Hyun-Joon Ha、Jung Woon Yang

  DOI：10.1002/chem.201706161

  日期：2018.2.16

  organocatalyst (2R)‐ or (2S)‐[diphenyl(trimethylsilyloxy)methyl]pyrrolidine as organocatalyst. The regioselective ring opening of aziridines and epoxides enabled us to achieve the highly efficient asymmetric synthesis of the antibiotic edeine D fragment 3‐hydroxy‐4,5‐diaminopenatanoic acid, an intermediate for the formal synthesis of non‐proteinogenic amino acid (−)‐galantinic acid, and for potent

  合成有价值的手性（氮丙啶-2-基）环氧乙烷基-3- carbaldehydes轴承从（氮丙啶-2-基）acrylaldehydes与H的立体选择性环氧化反应制备三个连续的官能团，包括氮丙啶，环氧化物，和醛2 ö 2使用有机催化剂（ 2 R）‐或（2 S）-[二苯基（三甲基甲硅烷基氧基）甲基]吡咯烷作为有机催化剂。氮丙啶和环氧化物的区域选择性开环使我们能够实现抗生素乙二胺D片段3-羟基-4,5-二氨基戊二酸的高效不对称合成，这是非蛋白原氨基酸（-）-正式合成的中间体没食子酸，强效抗真菌药（+）-普鲁斯汀以及医学上重要的构架3-羟基-2-羟甲基吡咯烷。
• Antibacterial 3,5-diaminopiperidine-substituted aromatic and heteroaromatic compounds
  申请人：Zhou Yuefen

  公开号：US20070197533A1

  公开（公告）日：2007-08-23

  The invention relates to antibacterial 3,5-diaminopiperidine-substituted aromatic and heteroaromatic compounds and pharmaceutical compositions thereof. This invention also relates to a method of using such compounds in the treatment of bacterial infections in mammals, especially humans.

  本发明涉及抗菌性3,5-二氨基哌啶取代的芳香和杂环化合物及其制药组合物。本发明还涉及使用这些化合物治疗哺乳动物（尤其是人类）细菌感染的方法。
• 7-substituted 1-aryl-naphthyridine-3-carboxylic acid amides and use thereof
  申请人：Bayer Aktiengesellschaft

  公开号：US10927109B2

  公开（公告）日：2021-02-23

  The present application relates to novel 7-substituted 1-arylnaphthyridine-3-carboxamides, to processes for their preparation, to their use, alone or in combinations, for the treatment and/or prevention of diseases, and to their use for the production of medicaments for the treatment and/or prevention of diseases, in particular for the treatment and/or prevention of cardiovascular disorders and/or renal disorders.

  本申请涉及新型 7-取代 1-芳基萘啶-3-羧酰胺、其制备工艺、其单独或组合用于治疗和/或预防疾病的用途，以及其用于生产治疗和/或预防疾病，特别是治疗和/或预防心血管疾病和/或肾脏疾病的药物。
• Asymmetric intramolecular amidation of N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine. A new entry to chiral building blocks for the synthesis of biologically active nitrogen-containing compounds
  作者：Hiroki Takahata、Yasunori Banba、Mayumi Tajima、Takefumi Momose

  DOI：10.1021/jo00001a045

  日期：1991.1

  Sharpless reaction of racemic N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine (1) leads to both an asymmetric kinetic resolution to provide optically active 1, which was subsequently used for intramolecular amidomercuration, and asymmetric epoxidation followed by concomitant cyclization into optically active cis-3-hydroxy-2-(hydroxymethyl)pyrrolidine (3). Optically active 1 and 3 have been expediently used as chiral building blocks in the asymmetric synthesis of several biologically active natural products.