methyl (2S,4S,5S,6R)-5-acetamido-4-[tert-butyl(dimethyl)silyl]oxy-6-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-propoxymethyl]-2-methoxyoxane-2-carboxylate | 474801-28-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S,4S,5S,6R)-5-acetamido-4-[tert-butyl(dimethyl)silyl]oxy-6-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-propoxymethyl]-2-methoxyoxane-2-carboxylate
• CAS: 474801-28-0
• 化学式: C₂₅H₄₇NO₉Si
• 分子量: 533.735
• InChiKey: HFAQFZHVRRVCLW-KHMXZZJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 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：
  111
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  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]-propoxymethyl]-2-methoxyoxane-2-carboxylate 在 palladium on activated charcoal 、 Lindlar catalyst 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium azide 、 Dowex 50W (H+) 、 硫酸 、 四丁基氟化铵 、 氢气 、 乙酸酐 、 溶剂黄146 、 三甲氧基磷 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)-5-Acetylamino-4-guanidino-6-((R)-1-propoxy-propyl)-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：

  硫酸二丙酯 、 Methyl-5-(acetylamino)-4-O-(tert-butyldimethylsilyl)-3,5-dideoxy-8,9-O-isopropyliden-β-D-glycero-D-galacto-2-nonulopyranosidonsaeure-methylester 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (2S,4S,5S,6R)-5-acetamido-4-[tert-butyl(dimethyl)silyl]oxy-6-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-propoxymethyl]-2-methoxyoxane-2-carboxylate
  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.