methyl (2R,3R,4S)-3-acetamido-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-3,4-dihydro-2H-pyran-6-carboxylate | 475639-64-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2R,3R,4S)-3-acetamido-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 475639-64-6
• 化学式: C₂₄H₄₀N₄O₁₁
• 分子量: 560.602
• InChiKey: JHPNRFUIZVSLFS-QBBQCFRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  203.34
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl (2R,3R,4S)-3-acetamido-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-3,4-dihydro-2H-pyran-6-carboxylate 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 5-acetamido-4-guanidino-2,3,4,5-tetradeoxy-7-methoxy-D-glycero-D-galacto-non-2-enopyranosoic acid trifluoroacetic acid salt
  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：

  (4S,5R,6R,1'S,2'R)-5-acetylamino-4-azido-6-(2',3'-diacetoxy-1'-methoxy)propyl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 在 Lindlar catalyst 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 methyl (2R,3R,4S)-3-acetamido-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-3,4-dihydro-2H-pyran-6-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