5'-deoxyisofagomine | 780782-20-9

• 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: 5'-deoxyisofagomine
• 英文别名: 3,4-Piperidinediol, 5-methyl-, (3R,4R,5S)-；(3R,4R,5S)-5-methylpiperidine-3,4-diol
• CAS: 780782-20-9
• 化学式: C₆H₁₃NO₂
• 分子量: 131.175
• InChiKey: WPRCMXASRHJGNG-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3R,4R,5S)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-vinylpiperidine 在 盐酸 、 三氟化硼乙醚 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 1.0h， 生成 5'-deoxyisofagomine
  参考文献：
  名称：

  A short and concise synthesis of isofagomine, homoisofagomine, and 5′-deoxyisofagomine

  摘要：

  A short and concise synthesis of isofagomine derivatives via the epoxidation of chiral N-Boc-5-hydroxy-3-piperidene, followed by regioselective epoxide ring opening is described. This constitutes the first reported synthesis of homoisofagomine and the 5'-deoxyisofagomine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.127

文献信息

• A New Route to Diverse 1-Azasugars from <i>N</i>-Boc-5-hydroxy-3-piperidene as a Common Building Block
  作者：Hidekazu Ouchi、Yukiko Mihara、Hiroki Takahata

  DOI：10.1021/jo050519j

  日期：2005.6.1

  for the synthesis of a variety of 1-azasugars with a nitrogen atom at the anomeric position is described. The readily available chiral N-Boc-5-hydroxy-3-piperidene 3 is transformed to isofagomine (2), homoisofagomine (13), and 5‘-deoxyisofagomine (14) via stereoselective epoxidation and regioselective ring-cleavage in a highly stereocontrolled manner. In addition, the synthesis of all four stereoisomers

  描述了一种合成具有异头位置氮原子的各种1-氮杂双胍的新的通用方法。易于获得的手性N -Boc-5-羟基-3-哌啶3通过立体选择性环氧化和区域选择性环裂解，以高度立体可控的方式转化为异黄花碱（2），高异黄花碱（13）和5'-脱氧异黄花碱（14）。 。此外，3,4,5- trihydroxypiperidines（所有四种立体异构体的合成18 - 21）被划分为1-azasugar型葡糖苷酶抑制剂是立体选择性地从（手性）啶实现3。
• Enantioselective Access to All-trans 5-Alkylpiperidine-3,4-diols: Application to the Asymmetric Synthesis of the 1-N-Iminosugar (+)-Isofagomine
  作者：Yves Génisson、Arnaud Rives、Vanessa Faugeroux、Nathalie Saffon、Michel Baltas

  DOI：10.1055/s-0029-1216935

  日期：2009.10

  that, after optimization of the ring-enlargement reaction conditions, could be efficiently transformed into the corresponding 3-hydroxypiperidines. This approach was applied to the asymmetric synthesis of (+)-isofagomine relying on regio- and stereoselective oxirane opening with the cyanide anion of a pivotal epoxypyrrolidine. iminosugar - piperidine - ring enlargement - epoxide opening

  描述了获得3，4-二取代的N-苄基脯氨醇衍生物，在优化环扩大反应条件之后，可以将其有效地转化为相应的3-羟基哌啶。该方法应用于（+）-异黄酮的不对称合成，其依赖于区域和立体选择性环氧乙烷的打开，并带有关键性环氧吡咯烷的氰化物阴离子。 亚氨基糖-哌啶-扩环-环氧开口
• C-Alkyl 5-membered ring imino sugars as new potent cytotoxic glucosylceramide synthase inhibitors
  作者：Vanessa Faugeroux、Yves Génisson、Nathalie Andrieu-Abadie、Sandra Colié、Thierry Levade、Michel Baltas

  DOI：10.1039/b613460b

  日期：——

  The stereoselective preparation of novel C-alkyl 5-membered ring imino sugars and their biological evaluation with regard to GCS inhibition and cytotoxicity in a murine melanoma model are reported.

  报告了新型 C- 烷基 5 元环亚胺糖的立体选择性制备及其在小鼠黑色素瘤模型中抑制 GCS 和细胞毒性的生物学评价。
• NEW METHOD FOR PREPARING ISOFAGOMINE AND ITS DERIVATIVES
  申请人：Rybczynski Philip

  公开号：US20100160638A1

  公开（公告）日：2010-06-24

  A method for preparing isofagomine, its derivatives, intermediates and salts thereof using novel processes to make isofagomine from D-(−)-arabinose and L-(−)-xylose.

  使用新的工艺从D-(−)-阿拉伯糖和L-(−)-木糖制备异法戈明、其衍生物、中间体和盐的方法。
• INHIBITORS OF GLUCOSYLCERAMIDE SYNTHASE FOR THE TREATMENT OF MOTOR NEURON DISEASES
  申请人：Institut du Cerveau et de la Moelle Épinière-ICM

  公开号：EP3318277A1

  公开（公告）日：2018-05-09

  The present invention relates to inhibitors of gangliosides metabolism for treating motor neuron diseases, in particular hereditary spastic paraplegias.

  本发明涉及用于治疗运动神经元疾病，特别是遗传性痉挛性截瘫的神经节苷脂代谢抑制剂。