(3R,4R,5R)-1-benzyl-3-(benzyloxy)-5-(hydroxymethyl)piperdin-4-ol | 215725-53-4

• 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,5R)-1-benzyl-3-(benzyloxy)-5-(hydroxymethyl)piperdin-4-ol
• 英文别名: (3R,4R,5R)-1-benzyl-3-benzyloxy-5-hydroxymethylpiperidin-4-ol；(3R,4R,5R)-1-benzyl-3-(benzyloxy)-5-(hydroxymethyl)piperidin-4-ol；(3R,4R,5R)-1-Benzyl-3-benzyloxy-5-hydroxymethylpiperidin4-ol；(3R,4R,5R)-1-benzyl-3-(hydroxymethyl)-5-phenylmethoxypiperidin-4-ol
• CAS: 215725-53-4
• 化学式: C₂₀H₂₅NO₃
• 分子量: 327.423
• InChiKey: KVHCGDBTLBVKMF-VAMGGRTRSA-N

物化性质

• 沸点：
  483.1±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-1-benzyl-3-(benzyloxy)-5-(hydroxymethyl)piperdin-4-ol 在 盐酸 、 二乙胺基三氟化硫 、 氢气 、 palladium(II) hydroxide 、 sodium hydride 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， -20.0~20.0 ℃ 、379.22 kPa 条件下， 反应 14.83h， 生成 (3R,4R,5S)-5-(fluoromethyl)piperidine-3,4-diol hydrochloride
  参考文献：
  名称：

  METHODS FOR PREVENTING AND/OR TREATING LYSOSOMAL STORAGE DISORDERS

  摘要：

  公开号：

  EP2416656B1
• 作为产物：
  描述：

  (3R,4R,5R)-5-(羟基甲基)哌啶-3,4-二醇盐酸盐 在 盐酸 、 sodium hydride 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 异丙醇 、 mineral oil 为溶剂， 反应 16.0h， 生成 (3R,4R,5R)-1-benzyl-3-(benzyloxy)-5-(hydroxymethyl)piperdin-4-ol
  参考文献：
  名称：

  METHODS FOR PREVENTING AND/OR TREATING LYSOSOMAL STORAGE DISORDERS

  摘要：

  公开号：

  EP2416656B1

文献信息

• Heterocyclic compounds
  申请人：Novo Nordisk A/S

  公开号：US06046214A1

  公开（公告）日：2000-04-04

  Novel piperidine compounds are provided, and those compounds are useful in the treatment and/or prevention of diabetes, and especially non-insulin dependent diabetes (NIDDM or type 2 diabetes) including overnight or meal treatment and treatment or prevention of longterm complications, such as retinopathy, neuropathy, nephropathy, and micro- and macroangiopathy; treatment of hyperglycemia, hypercholesterolemia, hypertension, hyperinsulinemia, hyperlipidemia, atherosclerosis or myocardial ischemia.

  提供了新型吡啶类化合物，这些化合物在治疗和/或预防糖尿病方面非常有用，尤其是非胰岛素依赖型糖尿病（NIDDM或2型糖尿病），包括过夜或餐后治疗，以及治疗或预防长期并发症，如视网膜病变、神经病变、肾病、微血管和大血管病变；治疗高血糖、高胆固醇血症、高血压、高胰岛素血症、高脂血症、动脉粥样硬化或心肌缺血。
• Azasugar derivatives, heparanase inhibitors, method for preparing same, compositions containing same, use thereof
  申请人：PETITOU Maurice

  公开号：US20070270354A1

  公开（公告）日：2007-11-22

  The invention concerns heparanase inhibiting compounds of general formula (I) wherein R represents a hydrogen atom, an hydroxyl radical, a —OSO 3 − radical, a —O—(C 1 -C 5 )alkyl radical or an —O— aralkyl radical; Z represents a COO − radical or a hydroxyl radical; X represents —OH or a saccharide unit of formula A, Y represents H, C 1 -C 5 alkyl or a saccharide unit of formula D; in free form or in the form of pharmaceutically acceptable salts formed with a base or an acid as well as in the form of solvates or hydrates. The derivatives of the invention are useful as medicines.

  该发明涉及通式（I）的肝素酶抑制化合物，其中R代表氢原子、羟基自由基、—OSO3−自由基、—O—（C1-C5）烷基自由基或—O—芳基烷基自由基；Z代表COO−自由基或羟基自由基；X代表—OH或通式A的糖单元；Y代表H、C1-C5烷基或通式D的糖单元；以游离形式或形成与碱或酸的药用可接受盐、溶剂化合物或水合物的形式存在。该发明的衍生物可用作药物。
• METHODS FOR PREVENTING AND/OR TREATING DEGENERATIVE DISORDERS OF THE CENTRAL NERVOUS SYSTEM
  申请人：Boyd Robert

  公开号：US20100261753A1

  公开（公告）日：2010-10-14

  The present invention provides methods for preventing and/or treating degenerative disorders of the central nervous system using 5-(fluoromethyl)piperidine-3,4-diol, 5-(chloromethyl)piperidine-3,4-diol, or a pharmaceutically acceptable salt, solvate, or prodrug thereof, or any combination of two or more thereof. In particular, the present invention provides methods for preventing and/or treating Parkinson's disease.

  本发明提供了使用5-(氟甲基)哌啶-3,4-二醇、5-(氯甲基)哌啶-3,4-二醇、或其药学上可接受的盐、溶剂或前药，或以上两种或以上的任意组合，预防和/或治疗中枢神经系统退行性疾病的方法。特别地，本发明提供了预防和/或治疗帕金森病的方法。
• Iminosugars: potential inhibitors of liver glycogen phosphorylase
  作者：Palle Jakobsen、Jane M Lundbeck、Marit Kristiansen、Jens Breinholt、Helle Demuth、Jan Pawlas、Maria P Torres Candela、Birgitte Andersen、Niels Westergaard、Karsten Lundgren、Naoki Asano

  DOI：10.1016/s0968-0896(00)00291-1

  日期：2001.3

  The first synthesis of the single isomers (3R,4R,5R); (3S,4S,5S); (3R,4R,5S) and (3S,4S,5R) of 5-hydroxymethyl-piperidine-3,4-diol from Arecolin is reported, including the synthesis of a series of N-substituted derivatives of the (3R,4R,5R)-isomer (Isofagomine). The inhibitory effect of these isomers as well as of a series of N-substituted derivatives of the (3R,4R,SR)-isomer and selected hydroxypiperidine analogues on liver glycogen phosphorylase (GP) showed that the (3R,4R,5R) configuration was essential for obtaining an inhibitory effect at submicromolar concentration. The results also showed that all three hydroxy groups should be present and could not be substituted, nor were extra OH groups allowed if sub-micromolar inhibition should be obtained. Some inhibitory effect was retained for N-substituted derivatives of Isofagagomine; however, N-substitution always resulted in a loss of activity compared to the parent compound, IC50 values ranging from 1 to 100 muM were obtained for simple alkyl, arylalkyl and benzoylmethyl substituents. Furthermore, we found that it was not enough to assure inhibitory effect to have the (R,,R) configuration. Fagomine, the (2R,3R,4R)-2-hydroxymethylpiperidine-3,4-diol analogue, showed an IC50 value of 200 muM compared to 0.7 muM for Isofagomine. In addition, Isofagomine was able to prevent basal and glucagon stimulated glycogen degradation in cultured hepatocytes with IC50 values of 2-3 muM. (C) 2001 Elsevier Science Ltd. All rights reserved.
• NOVEL HETEROCYCLIC COMPOUNDS
  申请人：NOVO NORDISK A/S

  公开号：EP0983239A1

  公开（公告）日：2000-03-08