(2S,4S,5R,6R)-5-Acetylamino-2-allyloxy-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid | 55560-08-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5R,6R)-5-Acetylamino-2-allyloxy-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid
• 英文别名: NeuAc(b)-O-allyl；(2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-prop-2-enoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 55560-08-2
• 化学式: C₁₄H₂₃NO₉
• 分子量: 349.338
• InChiKey: BWOMKFNRLLGJEU-DZXXBYIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R,6R)-5-Acetylamino-2-allyloxy-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid 、 甲醇 以95%的产率得到
  参考文献：
  名称：

  ROY, RENE;LAFERRIERE, CRAIG A., CAN. J. CHEM., 68,(1990) N1, C. 2045-2054

  摘要：

  DOI：
• 作为产物：
  描述：

  N-acetyl neuraminic acid 在 sodium hydroxide 、 乙酰氯 作用下， 反应 3.5h， 生成 (2S,4S,5R,6R)-5-Acetylamino-2-allyloxy-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  糖苷亲和配体的合成，用于纯化5'-单磷酸唾液酸合酶。

  摘要：

  DOI：

  10.1016/0008-6215(92)80046-4

文献信息

• Method and kits for the diagnosis of influenza
  申请人：Becton, Dickinson and Company

  公开号：US10317404B2

  公开（公告）日：2019-06-11

  Some embodiments provided herein relate to combined assays. In some embodiments, an assay for identifying influenza type A or influenza type B is combined with an assay for determining the sensitivity of an influenza neuraminidase to an antiviral drug.

  本文提供的一些实施方案涉及组合检测。在某些实施方案中，鉴定甲型或乙型流感的检测方法与确定流感神经氨酸酶对抗病毒药物敏感性的检测方法相结合。
• Methods and kits for the diagnosis of influenza
  申请人：Becton, Dickinson and Company

  公开号：US11209433B2

  公开（公告）日：2021-12-28

  Some embodiments provided herein relate to combined assays. In some embodiments, an assay for identifying influenza type A or influenza type B is combined with an assay for determining the sensitivity of an influenza neuraminidase to an antiviral drug.

  本文提供的一些实施方案涉及组合检测。在某些实施方案中，鉴定甲型或乙型流感的检测方法与确定流感神经氨酸酶对抗病毒药物敏感性的检测方法相结合。
• Synthesis of Methyl and Allyl alpha-Glycosides of N-Acetylneuraminic Acid in the Absence of Added Promoter.
  作者：Leonid O. Kononov、Göran Magnusson、Marina I. Ferrero、Cesare Rol、Giovanni V. Sebastiani、George W. Francis、József Szúnyog、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0141

  日期：——

  Sialic acids, especially N-acetylneuraminic acid, are present (as alpha-glycosides) on biologically important glycolipids and glycoproteins. Synthesis of sialic acid-containing oligosaccharides is therefore a prerequisite for many glycobiological studies. Such syntheses often use simple sialyl glycosides as starting materials. Their preparation usually employs heavy metal salts or other toxic and/or expensive promoters.' As a consequence, only few of these methods are suitable for large-scale preparations.We wish to report a simple, alpha/beta-selective, and high-yielding preparative procedure for the methyl sialosides 5 and 6, and the allyl sialoside 7 (Scheme 1), that avoids the use of specially added promoter (although HCl liberated during the reaction probably promotes the reaction). A few examples of 'non-catalyzed' glycosylations with acetobromohexosides, leading to de-O-acetylated methyl glycosides, have been reported.(2) Furthermore, various bromo analogs of 4 were recently used for sialylation of methanol and benzyl alcohol in the absence of metal salt promoters (but in the presence of collidinium salt) to give glycosides in 70-95% yield, with an alp ratio of 1:1-9:1.(3)The known O-acetylated N-acetylneuraminic acid(4) (1) and methyl ester(5,6) (2) were treated separately with HCl/CH2Cl2 to give acetochloroneuraminic acid(4) (3) and methyl ester(5) (4) of 90-95% purity according to H-1 NMR. Compounds 3 and 4 were each dissolved in methanol and the mixtures were kept at room temperature. According to TLC analysis, compound 3 was consumed within 1 min, whereas compound 4 required a reaction time of 1 h. Three different batches of methanol were investigated, with virtually identical results.
• METHODS AND KITS FOR THE DIAGNOSIS OF INFLUENZA
  申请人：Becton, Dickinson and Company

  公开号：EP2981618A1

  公开（公告）日：2016-02-10
• REAGENTS AND KITS FOR DETECTION OF INFLUENZA VIRUS AND THE LIKE
  申请人：LI Xing-Xiang

  公开号：US20080286758A1

  公开（公告）日：2008-11-20

  The present invention relates to reagents and methods for influenza virus detection. These reagents and methods disclosed in the present invention enable simple, rapid, specific and sensitive detection of influenza virus types A and B. These reagents are N-acetylneuraminic acid-firefly luciferin conjugates which can be cleaved by influenza virus neuraminidase.