(4S,5R,6R)-5-Acetylamino-6-((2R,3R,4R)-3,4-dihydroxy-oxepan-2-yl)-4-guanidino-5,6-dihydro-4H-pyran-2-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (4S,5R,6R)-5-Acetylamino-6-((2R,3R,4R)-3,4-dihydroxy-oxepan-2-yl)-4-guanidino-5,6-dihydro-4H-pyran-2-carboxylic acid
• 英文别名: (2R,3R,4S)-3-acetamido-2-[(2R,3R,4R)-3,4-dihydroxyoxepan-2-yl]-4-guanidino-3,4-dihydro-2H-pyran-6-carboxylic acid；(2R,3R,4S)-3-acetamido-4-(diaminomethylideneamino)-2-[(2R,3R,4R)-3,4-dihydroxyoxepan-2-yl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• 化学式: C₁₅H₂₄N₄O₇
• 分子量: 372.378
• InChiKey: LFDKEZTWZMJKBO-XAPBCISGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  190
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  Methyl-5-(acetylamino)-4-O-(tert-butyldimethylsilyl)-3,5-dideoxy-8,9-O-isopropyliden-β-D-glycero-D-galacto-2-nonulopyranosidonsaeure-methylester 在 Lindlar's catalyst 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 四氧化锇 、 Grubbs catalyst first generation 、 sodium azide 、 Dowex 50W (H⁺) 、 硫酸 、 四丁基氟化铵 、 氢气 、 sodium hydride 、 溶剂黄146 、 N-甲基吗啉氧化物 、 三氟乙酸 、 三甲氧基磷 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 2.0h， 生成 (4S,5R,6R)-5-Acetylamino-6-((2R,3R,4R)-3,4-dihydroxy-oxepan-2-yl)-4-guanidino-5,6-dihydro-4H-pyran-2-carboxylic acid
  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.