methyl (2R,3R,4S)-3-acetamido-2-((1R,2S)-1-azido-2,3-dihydroxypropyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-3,4-dihydro-2H-pyran-6-carboxylate | 475639-66-8

• 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-2-((1R,2S)-1-azido-2,3-dihydroxypropyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 475639-66-8
• 化学式: C₂₃H₃₇N₇O₁₀
• 分子量: 571.588
• InChiKey: AJVBXFHYKNUEAL-IHWGESPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  242.87
• 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-2-((1R,2S)-1-azido-2,3-dihydroxypropyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-3,4-dihydro-2H-pyran-6-carboxylate 在 Lindlar's catalyst 氢气 作用下， 以 乙醇 为溶剂， 以80%的产率得到methyl (2S,3R,4S)-3-acetamido-2-((1R,2S)-1-amino-2,3-dihydroxypropyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-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
• 作为产物：
  描述：

  N-((1R,2S,3R,4S,5R)-2-Fluoro-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl)-acetamide 在 Lindlar catalyst 盐酸 、 sodium azide 、 N-acetylneuraminic acid aldolase 、 Dowex 50W (H+) 、 硫酸 、 氢气 、 sodium methylate 、 sodium acetate 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (2R,3R,4S)-3-acetamido-2-((1R,2S)-1-azido-2,3-dihydroxypropyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-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