methyl (2R,4S,5R,6R)-5-acetamido-6-[(1R,2R)-1,2-dihydroxy-3-(4-methylphenyl)sulfonyloxypropyl]-4-hydroxy-2-prop-2-enoxyoxane-2-carboxylate | 1313497-68-5

• 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-(4-methylphenyl)sulfonyloxypropyl]-4-hydroxy-2-prop-2-enoxyoxane-2-carboxylate
• CAS: 1313497-68-5
• 化学式: C₂₂H₃₁NO₁₁S
• 分子量: 517.554
• InChiKey: KKGGMNPTQILVJG-ZJGVECAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  186
• 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-(4-methylphenyl)sulfonyloxypropyl]-4-hydroxy-2-prop-2-enoxyoxane-2-carboxylate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以68%的产率得到methyl (allyl 5-acetamido-8,9-anhydro-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  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：

  Methyl (allyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 、 对甲苯磺酰氯 在 吡啶 作用下， 以59%的产率得到methyl (2R,4S,5R,6R)-5-acetamido-6-[(1R,2R)-1,2-dihydroxy-3-(4-methylphenyl)sulfonyloxypropyl]-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.