(3S,4R,5S)-5-azido-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4,5-trihydroxypiperidine | 1294499-31-2

• 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: (3S,4R,5S)-5-azido-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4,5-trihydroxypiperidine
• 英文别名: tert-butyl (3aS,7S,7aR)-7-azido-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridine-5-carboxylate
• CAS: 1294499-31-2
• 化学式: C₁₃H₂₂N₄O₄
• 分子量: 298.342
• InChiKey: YJBAZIYJBUVURZ-LPEHRKFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S)-5-azido-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4,5-trihydroxypiperidine 在 palladium on carbon 、 氢气 作用下， 以 乙醇 为溶剂， 以75%的产率得到(3S,4R,5S)-5-amino-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4,5-trihydroxypiperidine
  参考文献：
  名称：

  作为新型亚氨基糖核苷类似物的核碱基二羟基哌啶基衍生物的合成与构象

  摘要：

  开发了一种用于合成重要手性支架 (3S,4R,5R)-1-N-Boc-3,4-isopropylidene-3,4,5-trihydroxypiperidine 的优化方法。使用该中间体，完成了各种手性氨基二羟基哌啶的制备，并将它们转化为一系列非糖苷的六元氮杂核苷。制备的哌啶氮杂核苷的 NMR 构象分析显示偏爱椅子构象，在所有情况下核碱基都固定在赤道位置。

  DOI：

  10.1002/ejoc.201001610
• 作为产物：
  描述：

  (3S,4R,5R)-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4,5-trihydroxypiperidine 在 4-二甲氨基吡啶 、 叠氮化锂 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 (3S,4R,5S)-5-azido-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4,5-trihydroxypiperidine
  参考文献：
  名称：

  作为新型亚氨基糖核苷类似物的核碱基二羟基哌啶基衍生物的合成与构象

  摘要：

  开发了一种用于合成重要手性支架 (3S,4R,5R)-1-N-Boc-3,4-isopropylidene-3,4,5-trihydroxypiperidine 的优化方法。使用该中间体，完成了各种手性氨基二羟基哌啶的制备，并将它们转化为一系列非糖苷的六元氮杂核苷。制备的哌啶氮杂核苷的 NMR 构象分析显示偏爱椅子构象，在所有情况下核碱基都固定在赤道位置。

  DOI：

  10.1002/ejoc.201001610

文献信息

• Sugar Derivatives Comprising Sulfur-Containing Moieties And Methods Of Making Same and Methods of Using the Same for the Treatment of MPS IIIC
  申请人：Amicus Therapeutics, Inc.

  公开号：US20150225420A1

  公开（公告）日：2015-08-13

  Described herein are modified sugar, iminosugar and azasugar compounds and methods of making same. One or more of these modified compounds contain sulfates, sulfites, sulfamates and/or sulfonamides. Also described are pharmaceutical compositions/formulations comprising these compounds, as well as methods using these modified sugar compounds for the treatment of MPS IIIC (also known as Sanfilippo Type C).
• Sugar Derivatives Comprising Sulfur-Containing Moieties And Methods Of Making Same And Methods Of Using The Same For The Treatment Of MPS IIIC
  申请人：Amicus Therapeutics, Inc.

  公开号：US20170190665A1

  公开（公告）日：2017-07-06

  Described herein are modified sugar, iminosugar and azasugar compounds and methods of making same. One or more of these modified compounds contain sulfates, sulfites, sulfamates and/or sulfonamides. Also described are pharmaceutical compositions/formulations comprising these compounds, as well as methods using these modified sugar compounds for the treatment of MPS IIIC (also known as Sanfilippo Type C).
• US9598438B2
  申请人：——

  公开号：US9598438B2

  公开（公告）日：2017-03-21
• [EN] SUGAR DERIVATIVES COMPRISING SULFUR-CONTAINING MOIETIES AND METHODS OF MAKING SAME AND METHODS OF USING THE SAME FOR THE TREATMENT OF MPS IIIC<br/>[FR] DÉRIVÉS DE SUCRE COMPRENANT DES FRACTIONS CONTENANT DU SOUFRE, LEURS PROCÉDÉS DE PRÉPARATION ET LEURS MÉTHODES D'UTILISATION POUR LE TRAITEMENT DE LA MPS IIIC
  申请人：AMICUS THERAPEUTICS INC

  公开号：WO2015123385A1

  公开（公告）日：2015-08-20

  Described herein are modified sugar, iminosugar and azasugar compounds and methods of making same. One or more of these modified compounds contain sulfates, sulfites, sulfamates and/or sulfonamides. Also described are pharmaceutical compositions/formulations comprising these compounds, as well as methods using these modified sugar compounds for the treatment of MPS IIIC (also known as Sanfilippo Type C).
• The Synthesis and Conformation of Dihydroxypiperidinyl Derivates of Nucleobases as Novel Iminosugar Nucleoside Analogs
  作者：Dominik Rejman、Radek Pohl、Martin Dračínský

  DOI：10.1002/ejoc.201001610

  日期：2011.4

  An optimized method for the synthesis of an important chiral scaffold, (3S,4R,5R)-1-N-Boc-3,4-isopropylidene-3,4,5-trihydroxypiperidine, was developed. Using this intermediate, the preparation of various chiral aminodihydroxypiperidines and their transformation into a series of non-glycosidic, six-membered azanucleosides was accomplished. NMR conformation analysis of the prepared piperidine azanucleosides

  开发了一种用于合成重要手性支架 (3S,4R,5R)-1-N-Boc-3,4-isopropylidene-3,4,5-trihydroxypiperidine 的优化方法。使用该中间体，完成了各种手性氨基二羟基哌啶的制备，并将它们转化为一系列非糖苷的六元氮杂核苷。制备的哌啶氮杂核苷的 NMR 构象分析显示偏爱椅子构象，在所有情况下核碱基都固定在赤道位置。