(4S,5R,6R)-5-Acetylamino-4-azido-6-((1S,2R)-2,3-diacetoxy-1-cyclohexylmethoxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester | 474801-58-6

• 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: (4S,5R,6R)-5-Acetylamino-4-azido-6-((1S,2R)-2,3-diacetoxy-1-cyclohexylmethoxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,3R,4S)-3-acetamido-4-azido-2-[(1S,2R)-2,3-diacetyloxy-1-(cyclohexylmethoxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 474801-58-6
• 化学式: C₂₃H₃₄N₄O₉
• 分子量: 510.544
• InChiKey: LOIRGOJPSXOPAV-PQZYZXGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (4S,5R,6R)-5-Acetylamino-4-azido-6-((1S,2R)-2,3-diacetoxy-1-cyclohexylmethoxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 在 Lindlar catalyst sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 (4S,5R,6R)-5-Acetylamino-6-((1R,2R)-1-cyclohexylmethoxy-2,3-dihydroxy-propyl)-4-guanidino-5,6-dihydro-4H-pyran-2-carboxylic acid; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Synthesis and anti-Influenza virus activity of 7-O-Alkylated derivatives related to zanamivir

  摘要：

  A series of 7-alkyl ether derivatives related to zanamivir were synthesized using direct alkylation of the C-7 alcohol of sialic acid. Alkyl ether moiety of less than 12 carbons in length showed low nanomolar inhibitory activity against influenza A virus sialidase. Furthermore, their moiety improved influenza A virus plaque reduction activity compared to zanamivir. However, removal of the 8,9-diol of the 7-O-alkyl derivatives resulted in loss of antiviral potency. This result suggests that 8,9-diol must play an important role in binding with both influenza A and B virus sialidases. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00329-3
• 作为产物：
  描述：

  (2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-cyclohexylmethoxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 sodium azide 、 Dowex 50W (H+) 、 硫酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (4S,5R,6R)-5-Acetylamino-4-azido-6-((1S,2R)-2,3-diacetoxy-1-cyclohexylmethoxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and anti-Influenza virus activity of 7-O-Alkylated derivatives related to zanamivir

  摘要：

  A series of 7-alkyl ether derivatives related to zanamivir were synthesized using direct alkylation of the C-7 alcohol of sialic acid. Alkyl ether moiety of less than 12 carbons in length showed low nanomolar inhibitory activity against influenza A virus sialidase. Furthermore, their moiety improved influenza A virus plaque reduction activity compared to zanamivir. However, removal of the 8,9-diol of the 7-O-alkyl derivatives resulted in loss of antiviral potency. This result suggests that 8,9-diol must play an important role in binding with both influenza A and B virus sialidases. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00329-3