(4R,5R,6R)-4-Acetoxy-5-acetylamino-6-(phenethyl-propyl-carbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester | 343934-38-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4R,5R,6R)-4-Acetoxy-5-acetylamino-6-(phenethyl-propyl-carbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,3R,4R)-3-acetamido-4-acetyloxy-2-[2-phenylethyl(propyl)carbamoyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 343934-38-3
• 化学式: C₂₃H₃₀N₂O₇
• 分子量: 446.5
• InChiKey: LYPZILMHKOJFDX-HMXCVIKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R,5R,6R)-4-Acetoxy-5-acetylamino-6-(phenethyl-propyl-carbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 水 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (5R,6R)-5-Acetylamino-6-(phenethyl-propyl-carbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid
  参考文献：
  名称：

  Sialidase inhibitors related to zanamivir. Further SAR studies of 4-amino-4H-pyran-2-carboxylic acid-6-propylamides

  摘要：

  SAR investigations of the 4- and 5-positions of a series of 4-amino-4H-pyran-2-carboxylic acid 6-carboxamides are reported. Potent inhibitors of influenza A sialidase with marked selectivity over the influenza B enzyme were obtained when the basic 4-amino substituent was replaced by hydroxyl or even deleted. Modifications at the 5-position exhibited a tight steric requirement, with trifluoroacetamide being optimal. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00019-1
• 作为产物：
  描述：

  (4R,5S,6R)-5-Acetylamino-4-(tert-butyl-diphenyl-silanyloxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 在 吡啶 、 甲醇 、 sodium chlorite 、 sodium periodate 、 四丁基氟化铵 、 水 、 sodium methylate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 叔丁醇 为溶剂， 生成 (4R,5R,6R)-4-Acetoxy-5-acetylamino-6-(phenethyl-propyl-carbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Sialidase inhibitors related to zanamivir. Further SAR studies of 4-amino-4H-pyran-2-carboxylic acid-6-propylamides

  摘要：

  SAR investigations of the 4- and 5-positions of a series of 4-amino-4H-pyran-2-carboxylic acid 6-carboxamides are reported. Potent inhibitors of influenza A sialidase with marked selectivity over the influenza B enzyme were obtained when the basic 4-amino substituent was replaced by hydroxyl or even deleted. Modifications at the 5-position exhibited a tight steric requirement, with trifluoroacetamide being optimal. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00019-1