(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-methoxy-6-((R)-1-pentyloxy-allyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 474802-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-methoxy-6-((R)-1-pentyloxy-allyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 474802-01-2
• 化学式: C₂₀H₃₃NO₈
• 分子量: 415.484
• InChiKey: AMKSKQMAPUFUNI-GJNTUIEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  29.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  109.39
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-methoxy-6-((R)-1-pentyloxy-allyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 palladium on activated charcoal 硫酸 、 氢气 、 乙酸酐 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 (4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((R)-1-pentyloxy-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
• 作为产物：
  描述：

  (2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentyloxy-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 三甲氧基磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-methoxy-6-((R)-1-pentyloxy-allyl)-tetrahydro-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