2,3-dehydroneuraminic acid | 41976-42-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-dehydroneuraminic acid
• 英文别名: 5-amino-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enoic acid；5-ammonio-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate；5-amino-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonic acid；Neu2en；2-Deoxy-2,3-dehydroneuraminsaeure；(2R,3R,4S)-3-amino-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS: 41976-42-5
• 化学式: C₉H₁₅NO₇
• 分子量: 249.221
• InChiKey: FCPYDHZOFFVRHL-LRGKAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  154
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3-dehydroneuraminic acid 在 Dowex 50WX₈, H⁺ 作用下， 以 甲醇 、 水 为溶剂， 反应 36.5h， 生成 methyl 4-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-5-(tert-butanamido)-3,4,5-trideoxy-D-glycero-D-galactonon-2-enonate
  参考文献：
  名称：

  使用其 N-全氟酰化同系物作为关键工具轻松非对映选择性进入 Neu5Ac2en 糖基的 4β-酰酰胺化

  摘要：

  通过使用相应的 N-全氟酰化同源物作为关键工具，Neu5Ac 的 N-酰化糖基的 4β-酰化的有效方案已被开发并应用于结合分子特征和抗病毒特性的糖基的合成。

  DOI：

  10.1002/ejoc.201200151
• 作为产物：
  描述：

  N-acetyl-D-mannosamine 在 CMP-唾液酸合成酶 、 Pasteurella multocida sialic acid aldolase 、 Pasteurella multocida sialyltransferase 1 mutant 、 胞苷-5’-三磷酸 、 sodium hydroxide 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 反应 12.0h， 生成 2,3-dehydroneuraminic acid
  参考文献：
  名称：

  [EN] SIALIDASE INHIBITORS AND PREPARATION THEREOF
  [FR] INHIBITEURS DE SIALIDASE ET LEUR PRÉPARATION

  摘要：

  公开号：

  WO2018201058A3

文献信息

• Synthesis of Oligomers Derived from Amide-Linked Neuraminic Acid Analogues
  作者：Travis Q. Gregar、Jacquelyn Gervay-Hague

  DOI：10.1021/jo035312+

  日期：2004.2.1

  N-Fluoren-9-ylmethoxycarbonyl-protected sugar amino acids derived from α-O-methoxy- and 2,3-dehydroneuraminic acids have been prepared. Incorporation of these monomer units into solid-phase synthesis led to the efficient synthesis of two series of oligomers varying from one to eight units in length. The (1→5)-linked amides of 2,3-dehydroneuraminic acid were further subjected to hydrogenation giving a

  已经制备了由α - O-甲氧基-和2，3-脱氢尿嘧啶酸衍生的N-氟人-9-基甲氧基羰基保护的糖氨基酸。将这些单体单元结合到固相合成中导致有效合成长度从一到八个单元的两个系列的低聚物。将2，3-脱氢尿嘧啶酸的（1→5）-连接的酰胺进一步进行氢化，得到在异头碳处具有β-氢取代基的第三系列低聚物。
• Synthesis and chemical characterization of several perfluorinated sialic acid glycals and evaluation of their in vitro antiviral activity against Newcastle disease virus
  作者：P. Rota、N. Papini、P. La Rocca、M. Montefiori、F. Cirillo、M. Piccoli、R. Scurati、L. Olsen、P. Allevi、L. Anastasia

  DOI：10.1039/c7md00072c

  日期：——

  Synthesis and biological evaluation of some C-5 modified sialic acid glycals, epimerized or not at the C-4 position, as HN inhibitors of Newcastle Disease Virus (NDV).

  一些C-5修饰的唾液酸糖醛的合成和生物评价，C-4位置是否发生了表异构化，作为新城疫病毒(HN)抑制剂的评估。
• METHOD FOR MANUFACTURING NEURAMINIC ACID DERIVATIVES
  申请人：DAIICHI SANKYO COMPANY, LIMITED

  公开号：US20140018417A1

  公开（公告）日：2014-01-16

  A method for manufacturing a compound represented by the formula (13): wherein R 2 represents a C 1 -C 4 alkyl group and Ac represents an acetyl group, including reacting a compound represented by the following formula (12): wherein R 2 represents a C 1 -C 4 alkyl group, Ac represents an acetyl group and Boc represents a tert-butoxycarbonyl group, with water.

  一种制造化合物的方法，该化合物的化学式为（13）：其中R2代表C1-C4烷基，Ac代表乙酰基，包括将化学式为（12）的化合物与水反应，该化学式中R2代表C1-C4烷基，Ac代表乙酰基，Boc代表叔丁氧羰基。
• NEURAMINIC ACID DERIVATIVES
  申请人：DAIICHI SANKYO COMPANY, LIMITED

  公开号：US20150376156A1

  公开（公告）日：2015-12-31

  A compound represented by the following formula (I): wherein R 1 represents a C 1 -C 19 alkyl, R 2 represents a C 1 -C 4 alkyl and Ac represents an acetyl, the compound represented by the formula (I) is optionally contained with up to 10 wt. % of a compound represented by the following formula (II): having a chemical purity of 97 wt. % or higher, wherein in the case where the compound represented by the formula (II) is contained with the compound represented by formula (I), the chemical purity of the mixture of the compound represented by the formula (I) and the compound represented by the formula (II) is 97 wt. % or higher.

  以下式子（I）所代表的化合物：其中R1代表C1-C19烷基，R2代表C1-C4烷基，Ac代表乙酰基。式（I）所代表的化合物可以与以下式子（II）所代表的化合物以最高10重量％的含量混合：该化合物的化学纯度为97重量％或更高。在化合物（II）与式（I）所代表的化合物混合的情况下，化合物（I）和化合物（II）的混合物的化学纯度为97重量％或更高。
• 2,3-Didehydro-2-deoxysialic acids structurally varied at C-5 and their behaviour towards the sialidase from Vibrio cholerae
  作者：Erwin Schreiner、Erich Zbiral、Reinhard G. Kleineidam、Roland Schauer

  DOI：10.1016/0008-6215(92)84150-q

  日期：1992.9

  2,3-Didehydro-2-deoxy-N-trifluoroacetylneuraminic acid (5-trifluoroacetyl-Neu2en) (3) has been synthesised from Neu5Ac2en (1) by hydrazinolysis, to give Neu2en (2), followed by N-trifluoroacetylation. 2,3-Didehydro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranoson ic acid (Kdn2en, 8) and 5-azido-2,3-didehydro-2,3,5-trideoxy-D-glycero-D-galacto-2-nonu lopyranosonic acid (5-azido-5-deoxy-Kdn2en, 9) have been prepared from the acetylated methyl esters of Kdn (4) and 5-azido-5-deoxy-Kdn (5) via Zemplén saponification. The behaviour of the above 2,3-didehydro-2-deoxysialic acids towards Vibrio cholerae sialidase has been investigated.