N-acetyl-neuraminic acid methyl ester | 32766-94-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-acetyl-neuraminic acid methyl ester
• 英文别名: N-Acetyl-neuraminsaeure-methylester；methyl (4S,5R,6R,7S,8R)-5-acetamido-4,6,7,8,9-pentahydroxy-2-oxononanoate
• CAS: 32766-94-2
• 化学式: C₁₂H₂₁NO₉
• 分子量: 323.3
• InChiKey: UEZGLVWRLAIKFI-GWAIUBNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-acetyl-neuraminic acid methyl ester 在 silver perchlorate 、 溶剂黄146 、 silver carbonate 作用下， 生成 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-(2-propenyl)-D-erythro-L-manno-nononate
  参考文献：
  名称：

  Synthesis and inhibitory activity of sialic acid derivatives targeted at viral sialate-O-acetylesterases

  摘要：

  A series of sialosides modified at the 4- and 9-hydroxy group were synthesised and tested for inhibition of the viral haemagglutinin-esterase activity from various Orthomyxoviruses and Coronaviruses. While no inhibition of the sialate-4-O-acetylesterases from mouse hepatitis virus strain S or sialodacryoadenitis virus was found, a 9-O-methyl derivative displayed inhibitory activity against recombinant sialate-9-O-acetylesterase from influenza C virus. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.008
• 作为产物：
  描述：

  甲醇 、 N-乙酰神经氨酸 在 Dowex 50 x 8 (H⁽¹⁺⁾ form) 作用下， 反应 2.0h， 生成 N-acetyl-neuraminic acid methyl ester
  参考文献：
  名称：

  神经氨酸全-O-三甲基甲硅烷基无环酮肟衍生物的气液相色谱和质谱分析

  摘要：

  摘要N-乙酰神经氨酸和N-羟甲基神经氨酸的甲基和乙基酯的无环O-甲基和O-（三甲基甲硅烷基）酮肟的全-O-三甲基甲硅烷基衍生物，以及甲基的无环O-苄基酮肟合成了这些N-酰基神经氨酸的酯。另外，制备了无环O-三甲基甲硅烷基酮肟的全-O-三甲基甲硅烷基衍生物和N-乙酰基和N-羟甲基神经氨酸的三氘代甲基酯的O-三甲基甲硅烷基（15N）酮肟。为了比较，合成了两种N-酰基亚氨基尿酸的环状乙基酯的全-O-三甲基甲硅烷基衍生物，并通过气-液相色谱和气-液相色谱-质谱联用对所有化合物进行了研究。

  DOI：

  10.1016/s0008-6215(00)82581-1

文献信息

• Synthesis of 4-O-[3-(aryl)prop-2-ynyl]-Neu5Ac2en and its 4-epi-analogs modified at C-4 by Sonogashira coupling reaction
  作者：Kazuki Sato、Kiyoshi Ikeda、Takashi Suzuki、Shinya Aoyama、Naoyoshi Maki、Yasuo Suzuki、Masayuki Sato

  DOI：10.1016/j.tet.2007.05.049

  日期：2007.8

  To explore new inhibitors of the sialidase of human parainfluenza virus type 1 (hPIV-1), a series of novel Neu5Ac2en derivatives were synthesized. Thus, 8,9-O-isopropylidene-4-O-2-propynyl-Neu5Ac2en methyl ester 8 was subjected to a Sonogashira coupling reaction with a variety of heteroaryl halides to produce a series of 4-O-(3-heteroaryl-2-propynyl) compound 9. Treatment of 9 with 80% acetic acid followed by alkaline hydrolysis afforded deprotected Neu5Ac2en compounds. The 4-epi-analogs of this type of Neu5Ac2en were synthesized in a similar manner. Compound 5d showed the most potent inhibitory activity (IC50 1.2 mu M) against hPIV-1 sialidase. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and inhibitory activity of sialic acid derivatives targeted at viral sialate-O-acetylesterases
  作者：Mathew Stanley、Juliane Mayr、Wolfgang Huber、Reinhard Vlasak、Hansjörg Streicher

  DOI：10.1016/j.ejmech.2011.04.008

  日期：2011.7

  A series of sialosides modified at the 4- and 9-hydroxy group were synthesised and tested for inhibition of the viral haemagglutinin-esterase activity from various Orthomyxoviruses and Coronaviruses. While no inhibition of the sialate-4-O-acetylesterases from mouse hepatitis virus strain S or sialodacryoadenitis virus was found, a 9-O-methyl derivative displayed inhibitory activity against recombinant sialate-9-O-acetylesterase from influenza C virus. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Gas-liquid chromatography and mass-spectral analysis of per-O-trimethylsilyl acyclic ketoxime derivatives of neuraminic acid
  作者：Thomas P. Mawhinney、Michael A. Madson、Roy H. Rice、Milton S. Feather、Giulio J. Barbero

  DOI：10.1016/s0008-6215(00)82581-1

  日期：1982.6

  -acetyl- and N -glycolylneuraminic acid were prepared. For comparison, the per- O -trimethylsilyl derivatives of the cyclic ethyl esters of the two N -acylneuraminic acids were synthesized and all compounds were studied by gas-liquid chromatography and combined gas-liquid chromatography-mass spectrometry.

  摘要N-乙酰神经氨酸和N-羟甲基神经氨酸的甲基和乙基酯的无环O-甲基和O-（三甲基甲硅烷基）酮肟的全-O-三甲基甲硅烷基衍生物，以及甲基的无环O-苄基酮肟合成了这些N-酰基神经氨酸的酯。另外，制备了无环O-三甲基甲硅烷基酮肟的全-O-三甲基甲硅烷基衍生物和N-乙酰基和N-羟甲基神经氨酸的三氘代甲基酯的O-三甲基甲硅烷基（15N）酮肟。为了比较，合成了两种N-酰基亚氨基尿酸的环状乙基酯的全-O-三甲基甲硅烷基衍生物，并通过气-液相色谱和气-液相色谱-质谱联用对所有化合物进行了研究。