methyl (2S,4S,5S,6R)-5-acetamido-4-[tert-butyl(dimethyl)silyl]oxy-6-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-pent-4-enoxymethyl]-2-methoxyoxane-2-carboxylate | 374603-95-9

• 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]-pent-4-enoxymethyl]-2-methoxyoxane-2-carboxylate
• CAS: 374603-95-9
• 化学式: C₂₇H₄₉NO₉Si
• 分子量: 559.773
• InChiKey: HPGYOEQPFOLPGJ-UAVGPPOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 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]-pent-4-enoxymethyl]-2-methoxyoxane-2-carboxylate 在 Lindlar's catalyst 吡啶 、 4-二甲氨基吡啶 、 四氧化锇 、 Grubbs catalyst first generation 、 sodium azide 、 Dowex 50W (H⁺) 、 硫酸 、 四丁基氟化铵 、 氢气 、 溶剂黄146 、 N-甲基吗啉氧化物 、 三甲氧基磷 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 丙酮 、 叔丁醇 为溶剂， 生成 (4R,5R,6R)-5-Acetylamino-4-amino-6-((2S,3R,4R)-3,4-diacetoxy-oxepan-2-yl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir

  摘要：

  We synthesized bicyclic ether sialidase inhibitors Such as tetrahydro-furan-2-yl. tetrahydro-pyran-2-yL and oxepan-2-yl derivatives related to zanamivir. These compounds substituted by diol at the C-3' and C-4' positions resulted in the retention of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. Compound I la in particular showed comparable efficacy in vivo relative to that of oseltamivir phosphate. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01039-9
• 作为产物：
  描述：

  5-碘-1-戊烯 、 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]-pent-4-enoxymethyl]-2-methoxyoxane-2-carboxylate
  参考文献：
  名称：

  Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir

  摘要：

  We synthesized bicyclic ether sialidase inhibitors Such as tetrahydro-furan-2-yl. tetrahydro-pyran-2-yL and oxepan-2-yl derivatives related to zanamivir. These compounds substituted by diol at the C-3' and C-4' positions resulted in the retention of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. Compound I la in particular showed comparable efficacy in vivo relative to that of oseltamivir phosphate. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01039-9

文献信息

• Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir
  作者：Takeshi Masuda、Satoshi Shibuya、Masami Arai、Shuku Yoshida、Takanori Tomozawa、Akiko Ohno、Makoto Yamashita、Takeshi Honda

  DOI：10.1016/s0960-894x(02)01039-9

  日期：2003.2

  We synthesized bicyclic ether sialidase inhibitors Such as tetrahydro-furan-2-yl. tetrahydro-pyran-2-yL and oxepan-2-yl derivatives related to zanamivir. These compounds substituted by diol at the C-3' and C-4' positions resulted in the retention of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. Compound I la in particular showed comparable efficacy in vivo relative to that of oseltamivir phosphate. (C) 2003 Elsevier Science Ltd. All rights reserved.