(3R,4R)-3-Hydroxy-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester | 206111-42-4

• 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: (3R,4R)-3-Hydroxy-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester
• 英文别名: rel-1-(1,1-Dimethylethyl)(3R,4R)-3-hydroxy-1,4-piperidinedicarboxylate；(3R,4R)-3-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidine-4-carboxylic acid
• CAS: 206111-42-4
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: RIZCQEWQJRFDHL-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-苄基-3-氧杂-4-哌啶甲酸乙酯 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 氢气 、 sodium carbonate 、 蔗糖 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 30.0 ℃ 、607.95 kPa 条件下， 反应 122.5h， 生成 (3R,4R)-3-Hydroxy-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester
  参考文献：
  名称：

  A Study of Baker's Yeast Reduction of Piperidone-carboxylates.

  摘要：

  The stereoselective baker's yeast reduction of various N-protected piperidone-carboxylic acids have been studied, and the enantioselectivity was found to be widely dependent on whether fermenting or non-fermenting conditions were employed. Thus reaction of N-tert-butoxycarbonyl-4-oxopiperidine-3-carboxylic acid ethyl ester (6) with fermenting baker's yeast gave almost racemic N-tert-butoxycarbonyl-4-hydroxypiperidine-3-carboxylic acid ethyl ester (7), however, with complete diastereoselectivity. Reduction of 6 with non-fermenting yeast gave 7 with a 24-41% enantiomeric excess. Similarly, reduction of N-tert-butoxycarbonyl-3-oxopiperidine-4-carboxylic acid ethyl ester (17) with fermenting baker's yeast gave racemic N-tert-butoxycarbonyl-3-hydroxypiperidine-4-carboxylic acid ethyl ester [(+/-)-18] diastereoselectively. A convenient method for determining the enantiomeric excess of the hydroxypiperidine carboxylic acids derivatives was found in the reaction with Sanger's reagent followed by HPLC on a chiral column.

  DOI：

  10.3891/acta.chem.scand.52-0461

文献信息

• Imidazole-pyrazole derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US11390604B2

  公开（公告）日：2022-07-19

  The disclosure provides novel imidazole pyrazole derivatives having the general formula (I), and pharmaceutically acceptable salts thereof, wherein X1, RA and R3 to R7 are as described herein: Further provided are pharmaceutical compositions including the compounds, processes of manufacturing the compounds and methods of using the compounds as medicaments, in particular methods of using the compounds as antibiotics for the treatment or prevention of bacterial infections and resulting diseases.

  本公开提供了具有通式 (I) 的新型咪唑吡唑衍生物及其药学上可接受的盐类，其中 X1、RA 和 R3 至 R7 如本文所述： 还提供了包括这些化合物的药物组合物、制造这些化合物的工艺以及将这些化合物用作药物的方法，特别是将这些化合物用作抗生素以治疗或预防细菌感染及其引起的疾病的方法。
• PIPERIDINE OLIGOMERS AND COMBINATORIAL LIBRARIES THEREOF
  申请人：Phytera Symbion ApS

  公开号：EP1000030A1

  公开（公告）日：2000-05-17
• NOVEL IMIDAZOLE-PYRAZOLE DERIVATIVES
  申请人：Hoffmann-La Roche Inc.

  公开号：US20200290998A1

  公开（公告）日：2020-09-17

  The disclosure provides novel imidazole pyrazole derivatives having the general formula (I), and pharmaceutically acceptable salts thereof, wherein X 1 , R A and R 3 to R 7 are as described herein: Further provided are pharmaceutical compositions including the compounds, processes of manufacturing the compounds and methods of using the compounds as medicaments, in particular methods of using the compounds as antibiotics for the treatment or prevention of bacterial infections and resulting diseases.
• [EN] PIPERIDINE OLIGOMERS AND COMBINATORIAL LIBRARIES THEREOF<br/>[FR] OLIGOMERES DE PIPERIDINE ET BANQUES COMBINATOIRES DE CEUX-CI
  申请人：PHYTERA SYMBION APS

  公开号：WO1999003832A1

  公开（公告）日：1999-01-28

  (EN) The present invention relates to piperidine oligomers, methods for the preparation of piperidine oligomers and compound libraries thereof, and the use of piperidine oligomers as drug substances. The present invention also relates to the use of combinatorial libraries of piperidine oligomers for screening purposes. The oligomers have one of the general formulas (I) or (II). Each of the monomers (piperidine carboxylic acids) are linked via amide bonds. The piperidine monomers may carry substituents, particularly hydroxy, hydroxymethyl, and carboxy substituents. The oligomers may be prepared in libraries (arrays) of compounds especially suitable for screening purposes.(FR) L'invention concerne des oligomères de pipéridine, des procédés pour la préparation d'oligomères de pipéridine et des banques de composés de ceux-ci, ainsi que l'utilisation des oligomères de pipéridine en tant que substances médicamenteuses. L'invention concerne également l'utilisation de banques combinatoires d'oligomères de pipéridine à des fins de criblage. Les oligomères sont représentés par les formules générales I ou II. Chaque monomère (acides carboxyliques de pipéridine) est lié par des liaisons amide. Les monomères de pipéridine peuvent porter des substituants, particulièrement des substituants sélectionnés parmi hydroxy, hydroxyméthyle et carboxy. Les oligomères peuvent être préparés dans des banques (réseaux) de composés qui conviennent spécialement au criblage.
• A Study of Baker's Yeast Reduction of Piperidone-carboxylates.
  作者：Marianne Willert、Mikael Bols、Anders Hjelholt Pedersen、Palle Schneider、Louisa Barré、Ole Hammerich、Inger Søtofte、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0461

  日期：——

  The stereoselective baker's yeast reduction of various N-protected piperidone-carboxylic acids have been studied, and the enantioselectivity was found to be widely dependent on whether fermenting or non-fermenting conditions were employed. Thus reaction of N-tert-butoxycarbonyl-4-oxopiperidine-3-carboxylic acid ethyl ester (6) with fermenting baker's yeast gave almost racemic N-tert-butoxycarbonyl-4-hydroxypiperidine-3-carboxylic acid ethyl ester (7), however, with complete diastereoselectivity. Reduction of 6 with non-fermenting yeast gave 7 with a 24-41% enantiomeric excess. Similarly, reduction of N-tert-butoxycarbonyl-3-oxopiperidine-4-carboxylic acid ethyl ester (17) with fermenting baker's yeast gave racemic N-tert-butoxycarbonyl-3-hydroxypiperidine-4-carboxylic acid ethyl ester [(+/-)-18] diastereoselectively. A convenient method for determining the enantiomeric excess of the hydroxypiperidine carboxylic acids derivatives was found in the reaction with Sanger's reagent followed by HPLC on a chiral column.