5-acetamido-3,5-dideoxy-7-O-methyl-D-glycero-D-galacto-2-nonuropyranosoic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetamido-3,5-dideoxy-7-O-methyl-D-glycero-D-galacto-2-nonuropyranosoic acid
• 英文别名: NeuAc7Me；(4S,5R,6R)-5-acetamido-6-[(1R,2R)-2,3-dihydroxy-1-methoxypropyl]-2,4-dihydroxyoxane-2-carboxylic acid
• 化学式: C₁₂H₂₁NO₉
• 分子量: 323.3
• InChiKey: MPKYSTSWLKBQSZ-PQYSTZNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  5-acetamido-3,5-dideoxy-7-O-methyl-D-glycero-D-galacto-2-nonuropyranosoic acid 在 Lindlar catalyst sodium azide 、 Dowex 50W (H+) 、 硫酸 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (4S,5R,6R)-5-acetamido-4-amino-6-[(1S,2R)-2,3-diacetoxy-1-methoxy-propyl]-5,6-dihydro-4H-pyran-2-carboxylate
  参考文献：
  名称：

  Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives

  摘要：

  Substitution of 7-OH by small hydrophobic groups on zanamivir resulted in the retaining of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. These compounds were prepared by treatment of the corresponding 7-substituted sialic acids derived from 4-modified N-acetyl-D-mannosamine (ManNAc) using enzyme-catalyzed aldol condensation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00328-1
• 作为产物：
  描述：

  N-((1R,2S,3R,4S,5R)-3-Hydroxy-2-methoxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl)-acetamide 在 盐酸 、 N-acetylneuraminic acid aldolase 、 sodium acetate 、 三氟乙酸 作用下， 生成 5-acetamido-3,5-dideoxy-7-O-methyl-D-glycero-D-galacto-2-nonuropyranosoic acid
  参考文献：
  名称：

  Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives

  摘要：

  Substitution of 7-OH by small hydrophobic groups on zanamivir resulted in the retaining of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. These compounds were prepared by treatment of the corresponding 7-substituted sialic acids derived from 4-modified N-acetyl-D-mannosamine (ManNAc) using enzyme-catalyzed aldol condensation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00328-1

文献信息

• Neuraminic acid derivatives, their preparation and their medical use
  申请人：Sankyo Company, Limited

  公开号：US06340702B1

  公开（公告）日：2002-01-22

  Compounds of formula (I) or their salts or esters: have excellent sialidase inhibitory activity and are therefore useful for the treatment and prevention of influenza and other viral diseases where the replication of the virus is susceptible to sialidase inhibitors.

  化合物的结构式(I)或其盐或酯：具有出色的唾液酸酶抑制活性，因此可用于治疗和预防流感和其他病毒性疾病，其中病毒的复制易受唾液酸酶抑制剂的影响。
• [EN] METHOD FOR MANUFACTURING NEURAMINIC ACID DERIVATIVES<br/>[FR] PROCÉDÉ DE FABRICATION DE DÉRIVÉS DE L'ACIDE NEURAMINIQUE
  申请人：DAIICHI SANKYO CO LTD

  公开号：WO2008126943A2

  公开（公告）日：2008-10-23

  [EN] A method for manufacturing neuraminic acid derivatives is provided, also synthetic intermediates of the neuraminic acid derivatives and methods for their manufacture, and neuraminic acid derivatives having high purity. [Means for solution] A synthetic intermediate compound represented by the formula (7) is provided: [wherein R3 represents alkyl; R4 and R5 each represents H, alkyl, phenyl, or together represent tetramethylene, pentamethylene, oxo].
  [FR] L'invention se rapporte à un procédé de fabrication de dérivés de l'acide neuraminique, à des intermédiaires synthétiques de l'acide neuraminique et à des procédés de fabrication de ces derniers, et à des dérivés de l'acide neuraminique de grande pureté. L'invention concerne un composé d'intermédiaire synthétique représenté par la formule (7) : [dans laquelle R³ représente alkyle; R⁴ et R⁵ représentent chacun H, alkyle, phényle, ou représentent ensemble tétraméthylène, pentaméthylène, oxo].
• Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives
  作者：Takeshi Honda、Takeshi Masuda、Shuku Yoshida、Masami Arai、Yoshiyuki Kobayashi、Makoto Yamashita

  DOI：10.1016/s0960-894x(02)00328-1

  日期：2002.8

  Substitution of 7-OH by small hydrophobic groups on zanamivir resulted in the retaining of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. These compounds were prepared by treatment of the corresponding 7-substituted sialic acids derived from 4-modified N-acetyl-D-mannosamine (ManNAc) using enzyme-catalyzed aldol condensation. (C) 2002 Elsevier Science Ltd. All rights reserved.