(2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-[2-(2,2-diethyl-[1,3]dioxolan-4-yl)-ethoxy]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester | 548759-51-9

• 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)-[2-(2,2-diethyl-[1,3]dioxolan-4-yl)-ethoxy]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-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)-2-(2,2-diethyl-1,3-dioxolan-4-yl)ethoxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2-methoxyoxane-2-carboxylate
• CAS: 548759-51-9
• 化学式: C₃₁H₅₇NO₁₁Si
• 分子量: 647.879
• InChiKey: XICCOYBCYOEMIH-BGVJXYFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-[2-(2,2-diethyl-[1,3]dioxolan-4-yl)-ethoxy]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 Grubbs catalyst first generation 、 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 、 乙醇 、 二氯甲烷 为溶剂， 生成 (2R,3R,4S,2'R)-4-Acetoxy-3-acetylamino-3,4,3',4',5',6'-hexahydro-2H,2'H-[2,2']bipyranyl-6-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：

  3,3-dimethoxypentane 在 吡啶 、 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-[2-(2,2-diethyl-[1,3]dioxolan-4-yl)-ethoxy]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2-methoxy-tetrahydro-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

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.