(2R,3R,4R,5S)-2-[(acetyloxy)methyl]-piperidine-3,4,5-triol triacetate | 131262-75-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3R,4R,5S)-2-[(acetyloxy)methyl]-piperidine-3,4,5-triol triacetate
• 英文别名: tetra-O-acetyl-DNJ；2,3,4,6-tetra-O-acetyl-1-deoxynojirimycin；1,5-Dideoxy-1,5-imino-D-glucitol, tetraacetate；[(2R,3R,4R,5S)-3,4,5-triacetyloxypiperidin-2-yl]methyl acetate
• CAS: 131262-75-4
• 化学式: C₁₄H₂₁NO₈
• 分子量: 331.323
• InChiKey: KSJGYSFTFIWAQC-XJFOESAGSA-N

物化性质

• 沸点：
  380.1±35.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S)-2-[(acetyloxy)methyl]-piperidine-3,4,5-triol triacetate 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 1-脱氧野尻霉素
  参考文献：
  名称：

  由β-D-糖苷合成双脱氧和三脱氧亚氨基醛醇的一般方法。

  摘要：

  氨基糖（也称为氮杂糖）是一类重要的糖苷酶抑制剂，具有作为药物的巨大潜力，其中一类化合物的1，5-二甲氧基和1，5，6-三甲氧基亚氨基醛糖醇是其中的一员。它们的潜在治疗应用范围从糖尿病到癌症和艾滋病。我们在这里提出了一种从β-D-糖苷开始制备具有D-葡萄糖和D-半乳糖构型的化合物的一般方法。该方法特别具有吸引力，因为它具有很高的立体选择性和直接性。关键步骤是将糖苷选择性氧化为己磺酸，并将肟衍生物还原为内酰胺，然后将其进一步还原为目标化合物。如果C-6位带有乙酰氧基，则可以在还原过程中将其脱氧。然后产生三脱氧亚氨基糖。肟还原前的脱乙酰基产生双脱氧化合物。

  DOI：

  10.1016/s0008-6215(00)00124-5
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-5-hydroxy-β-D-glucopyranose 在 甲酸 、 氨 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 1.0h， 生成 (2R,3R,4R,5S)-2-[(acetyloxy)methyl]-piperidine-3,4,5-triol triacetate
  参考文献：
  名称：

  Exploiting angled thin film vortex microfluidics for expeditious syntheses of iminosugars

  摘要：

  氨基糖是碳水化合物治疗领域的重要化合物。涡流薄膜微流体反应器可有效合成此类化合物。

  DOI：

  10.1039/d2ra04409a

文献信息

• A derivatization procedure for the simultaneous analysis of iminosugars and other low molecular weight carbohydrates by GC–MS in mulberry (Morus sp.)
  作者：S. Rodríguez-Sánchez、O. Hernández-Hernández、A.I. Ruiz-Matute、M.L. Sanz

  DOI：10.1016/j.foodchem.2010.10.097

  日期：2011.5

  iminosugars such as deoxynojirimycin (DNJ) or fagomine and other carbohydrates of low molecular weight by gas chromatography coupled to mass spectrometry (GC–MS) in Morus sp. Both oximation + trimethylsilylation and oximation + acetylation allowed the separation of target compounds, whereas trimethylsilyl (TMS) and acetylated derivatives showed several coelutions. Nevertheless, oximation + acetylation were

  不同的衍生化过程中测定同时分析的亚氨基糖如脱氧野尻霉素（DNJ）或桑叶生物碱和低分子量的其它碳水化合物通过气相色谱法在耦合到质谱法（GC-MS）桑属。肟化+三甲基甲硅烷基化和肟化+乙酰化均可分离目标化合物，而三甲基甲硅烷基（TMS）和乙酰化衍生物则表现出几种共洗脱。然而，由于酮糖的不完全衍生化，由于给出的酮糖结果不准确，因此放弃了肟化+乙酰化。分析了转化为三甲基甲硅烷基肟（TMSO）的不同条件，使用六甲基二硅氮烷与三氟乙酸作为甲硅烷基化剂可获得最佳结果。亚氨基糖（DNJ，桑叶生物碱和哌可酸的衍生物）和其它碳水化合物如单糖和二糖的含量，肌醇和肌醇半乳糖苷的异构体在桑树提取物（水果，树叶和树枝）通过使用TMSO过程GC-MS来确定。
• 1,5-dideoxy-1,5-imino-D-glucitol derivatives
  申请人：G. D. Searle & Co.

  公开号：US05221746A1

  公开（公告）日：1993-06-22

  O-acylated derivatives of 1,5-dideoxy-1,5-imino-D-glucitol are disclosed that contain an N-alkyl or N-aroyl radical in which from one to four of the free hydroxyl groups are O-acylated with carboxylic alkanoyl radicals selected from the group consisting of .omega.,.omega.,.omega.-trifluoro alkanoyl having from three to eight carbon atoms, carboxylic cycloalkanoyl groups having from four to eight carbon atoms and carboxylic acyclic alkanoyl groups having from two to ten carbon atoms, wherein the N-aroyl radical is selected from the group consisting of p-decylbenzoyl, 3-(p-chlorophenoxy)propanoyl, 2-(acetyloxy)benzoyl, [1,1'-biphenyl]-4-ylcarbonyl, 2-thiopheneacetyl, trans-3-furanacryloyl 3-methoxyphenylacetyl and 3-(trifluoromethyl)benzoyl, and wherein the N-alkyl contains from one to fourteen carbon atoms, provided that when N-alkyl contains from one to five carbon atoms the O-acylated groups are .omega.,.omega.,.omega.-trifluoro alkanoyl or carboxylic cycloalkanoyl.

  披露了1,5-二去氧-1,5-亚胺-D-葡萄糖醇的O-酰化衍生物，其中含有一个到四个自由羟基被选自以下羧基烷酰基的羧基烷酰基的N-烷基或N-芳酰基，.omega.，.omega.，.omega.-三氟烷酰基，碳原子数为三至八个，具有四至八个碳原子的羧基环烷酰基和具有两至十个碳原子的羧基无环烷酰基，其中N-芳酰基选自以下羧基苯基，3-(对氯苯氧基)丙酰基，2-(乙酰氧基)苯甲酰基，[1,1'-联苯]-4-基甲酰基，2-噻吩乙酰基，反式-3-呋喃丙烯基3-甲氧基苯乙酰基和3-(三氟甲基)苯甲酰基，其中N-烷基含有一个到十四个碳原子，前提是当N-烷基含有一个到五个碳原子时，O-酰化基团为.omega.，.omega.，.omega.-三氟烷酰基或羧基环烷酰基。
• Antiviral compounds
  申请人：G. D. Searle & Co.

  公开号：US05310745A1

  公开（公告）日：1994-05-10

  A method of inhibiting lentivirus is disclosed which comprises mammalian host susceptible to said lentivirus with a virally inhibitory effective amount of an O-acylated derivative of 1,5-dideoxy-1,5-imino-D-glucitol and their N-alkyl, N-acyl and N-aroyl derivatives in which from one to four of the free hydroxyl groups are O-acylated with carboxylic alkanoyl radicals selected from the group consisting of .omega.,.omega.,.omega.-trifluoroalkanoyl having from three to eight carbon atoms, carboxylic cycloalkanoyl groups having from four to eight carbon atoms and carboxylic acyclic alkanoyl groups having from two to ten carbon atoms, wherein the N-aroyl groups contain from 7 to 14 carbon atoms, the N-acyl groups contain from 4 to 8 carbon atoms and the N-alkyl groups contain from 1 to 14 carbon atoms.

  本发明揭示了一种抑制慢病毒的方法，包括将哺乳动物宿主暴露于所述慢病毒的有效抑制量的1,5-二去氧-1,5-亚胺-D-葡萄糖醇的O-酰化衍生物及其N-烷基，N-酰基和N-芳酰衍生物中，其中从一个到四个自由羟基被选自由三至八个碳原子的羧基烷酰基的.omega.，.omega.，.omega.-三氟烷酰基，含有四至八个碳原子的环烷基羧基和含有两至十个碳原子的无环烷基羧基，其中N-芳酰基含有七至十四个碳原子，N-酰基含有四至八个碳原子，N-烷基含有一至十四个碳原子。
• 1,5-dideoxy-1,5-imino-d-glucitol derivatives
  申请人：G. D. Searle & Co.

  公开号：US05144037A1

  公开（公告）日：1992-09-01

  Antiviral O-acylated derivatives of 1,5-dideoxy-1,5-imino-D-glucitol are disclosed that contain an N-alkyl or N-aroyl radical in which from one to four of the free hydroxyl groups are O-acylated with carboxylic alkanoyl radicals selected from the group consisting of .omega.,.omega.,.omega.-trifluoro alkanoyl having from three to eight carbon atoms, carboxylic cycloalkanoyl groups having from four to eight carbon atoms and carboxylic acyclic alkanoyl groups having from two to ten carbon atoms, wherein the N-aroyl radical is selected from the group consisting of p-decylbenzoyl, 3-(p-chlorophenoxy)propanoyl, 2-(acetyloxy)benzoyl, [1,1'-biphenyl]-4-ylcarbonyl, 2-thiopheneacetyl, trans-3-furanacryloyl, 3-methoxyphenylacetyl and 3-(trifluoromethyl)benzoyl, and wherein the N-alkyl contains from one to fourteen carbon atoms, provided that when N-alkyl contains from one to five carbon atoms the O-acylated groups are .omega.,.omega.,.omega.-trifluoro alkanoyl or carboxylic cycloalkanoyl.

  本发明涉及1,5-二去氧-1,5-亚硝基-D-葡萄糖醇的抗病毒O-酰化衍生物，其中含有一个至四个游离羟基被选自由从三到八个碳原子的羧基脂肪酰基所选择的ω,ω,ω-三氟代烷酰基、从四到八个碳原子的环烷基羧基和从二到十个碳原子的非环烷基羧基的N-烷基或N-芳酰基，其中N-芳酰基被选自p-癸基苯甲酰基、3-(对氯苯氧基)丙酰基、2-(乙酰氧基)苯甲酰基、[1,1'-联苯]-4-基羰基、2-噻吩乙酰基、反式-3-呋喃丙烯酰基、3-甲氧基苯乙酰基和3-(三氟甲基)苯甲酰基，其中N-烷基含有从一个到十四个碳原子，但当N-烷基含有从一个到五个碳原子时，O-酰化基为ω,ω,ω-三氟代烷酰基或环烷基羧基。
• Method for treating a mammal infected with respiratory syncytial virus
  申请人：G. D. Searle & Co.

  公开号：US05622972A1

  公开（公告）日：1997-04-22

  A method is provided for treating a mammal infected with respiratory syncytial virus (RSV) comprising administering to the mammal an RSV inhibitory effective amount of a compound or its pharmaceutically acceptable salt of the formula ##STR1## wherein R.sup.1 is alkyl, aralkyl, aroyl or acyl and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are H or acyl.

  提供了一种治疗感染呼吸道合胞病毒（RSV）的哺乳动物的方法，包括向哺乳动物施用一种化合物或其药学上可接受的盐的RSV抑制有效量，该化合物的结构式为##STR1##其中R.sup.1是烷基，芳基甲基，芳酰基或酰基，R.sup.2、R.sup.3、R.sup.4和R.sup.5是H或酰基。