methyl (2R,4S,5R,6R)-5-acetamido-6-[(1R,2R)-1,2-dihydroxy-3-[methoxy(methyl)phosphoryl]oxypropyl]-4-hydroxy-2-prop-2-enoxyoxane-2-carboxylate | 1313497-69-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2R,4S,5R,6R)-5-acetamido-6-[(1R,2R)-1,2-dihydroxy-3-[methoxy(methyl)phosphoryl]oxypropyl]-4-hydroxy-2-prop-2-enoxyoxane-2-carboxylate
• CAS: 1313497-69-6
• 化学式: C₁₇H₃₀NO₁₁P
• 分子量: 455.399
• InChiKey: SFKQXCGYILRJOR-IBJXSWJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  170
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (2R,4S,5R,6R)-5-acetamido-6-[(1R,2R)-1,2-dihydroxy-3-[methoxy(methyl)phosphoryl]oxypropyl]-4-hydroxy-2-prop-2-enoxyoxane-2-carboxylate 在 吡啶 、 水 、 苯硫酚 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 98.0h， 生成 azanium;[(2R,3R)-3-[(2R,3R,4S,6R)-3-acetamido-6-carboxy-4-hydroxy-6-prop-2-enoxyoxan-2-yl]-2,3-dihydroxypropoxy]-methylphosphinate
  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：

  甲基氯膦酸甲酯 、 Methyl (allyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到methyl (2R,4S,5R,6R)-5-acetamido-6-[(1R,2R)-1,2-dihydroxy-3-[methoxy(methyl)phosphoryl]oxypropyl]-4-hydroxy-2-prop-2-enoxyoxane-2-carboxylate
  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

文献信息

• 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.