(2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-(2-hydroxy-ethoxy)-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester | 474801-77-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-(2-hydroxy-ethoxy)-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,4S,5S,6R)-5-acetamido-4-[tert-butyl(dimethyl)silyl]oxy-6-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-(2-hydroxyethoxy)methyl]-2-methoxyoxane-2-carboxylate
• CAS: 474801-77-9
• 化学式: C₂₄H₄₅NO₁₀Si
• 分子量: 535.708
• InChiKey: OAFRSTSRZHWXSW-YHVPBLTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-(2-hydroxy-ethoxy)-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 Lindlar catalyst 吡啶 、 sodium hydroxide 、 sodium azide 、 Dowex 50W (H+) 、 硫酸 、 氢气 、 sodium methylate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4S,5R,6R,1'R,2'R)-5-acetylamino-6-[1'-(2''-aminoethyloxy)-2',3'-dihydroxy]propyl-5,6-dihydro-4-guanidino-4H-pyran-2-carboxylic acid trilfluoroacetate
  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：

  methyl (2S,4S,5S,6R)-5-acetamido-4-[tert-butyl(dimethyl)silyl]oxy-6-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-(2-phenylmethoxyethoxy)methyl]-2-methoxyoxane-2-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以80%的产率得到(2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-(2-hydroxy-ethoxy)-methyl]-2-methoxy-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

文献信息

• Synthesis and anti-Influenza virus activity of 7-O-Alkylated derivatives related to zanamivir
  作者：Takeshi Honda、Takeshi Masuda、Shuku Yoshida、Masami Arai、Satoru Kaneko、Makoto Yamashita

  DOI：10.1016/s0960-894x(02)00329-3

  日期：2002.8

  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.