(2S)-2-[[(2R,3S,4S)-2-amino-5-carbamoyloxy-3,4-dihydroxypentanoyl]amino]-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]acetic acid | 1174272-50-4

• 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: (2S)-2-[[(2R,3S,4S)-2-amino-5-carbamoyloxy-3,4-dihydroxypentanoyl]amino]-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]acetic acid
• CAS: 1174272-50-4
• 化学式: C₁₇H₂₅N₅O₁₂
• 分子量: 491.412
• InChiKey: MUIVXLDDXLZVGN-ZEANYMOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.4
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  284
• 氢给体数：
  9
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  在 lithium hydroxide 、 水 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 (2S)-2-[[(2R,3S,4S)-2-amino-5-carbamoyloxy-3,4-dihydroxypentanoyl]amino]-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]acetic acid
  参考文献：
  名称：

  An asymmetric approach to 5-O-carbamoyl-2-epi-polyoxamic acid and the total synthesis of 2′′-epi-polyoxin J

  摘要：

  A stereospecific synthetic approach to 5-O-carbamoyl-2-epi-polyoxamic acid has been developed. The asymmetric nucleophilic addition of 2-lithiofuran to a tert-butanesulfinyl imine was employed as the key step to construct the C-2 stereocenter and 2 ''-epi-polyoxin J has been synthesized for the first time. Significantly, the synthesis provides a facile method for the large scale and stereoselective preparation of 5-O-carbamoyl-2-epi-polyoxamic acid and some related diastereoisomers of polyoxins and its analogues because of its simple operation, excellent yield, and high stereoselectivity. This will be convenient for research of the polyoxins' structure-activity relationship and to search for more potent and effective anti-candidal agents. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.033