3,4-dideoxy-4-fluoro-L-glycero-tetronic acid | 286856-69-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3,4-dideoxy-4-fluoro-L-glycero-tetronic acid
• 英文别名: (2S)-4-fluoro-2-hydroxybutanoic acid
• CAS: 286856-69-7
• 化学式: C₄H₇FO₃
• 分子量: 122.096
• InChiKey: SEVCNPDIXFSYCF-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-amino-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside 、 3,4-dideoxy-4-fluoro-L-glycero-tetronic acid 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以53%的产率得到methyl 4,6-dideoxy-4-(3,4-dideoxy-4-fluoro-L-glycero-tetronamido)-2-O-methyl-α-D-mannopyranoside
  参考文献：
  名称：

  Syntheses of fluorinated ligands to probe binding of antigenic determinants of Vibrio cholerae O:1, serotypes Inaba and Ogawa, to antibodies

  摘要：

  Derivatives of methyl alpha-glycosides of antigenic determinants of Vibrio cholerae O:1, serotypes Inaba and Ogawa, specifically Fluorinated at position 2' or 4' have been synthesized by coupling the appropriately fluorinated derivatives of 3-deoxy-L-glycero-tetronic acid with the methyl oc-glycosides of perosamine. The compound having the fluorine atom at position 2 was obtained by electrophilic addition of fluorine to the glycal derived from the parent antigenic determinant, serotypes Inaba, using Selectfluor(TM) as a fluorination reagent. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00505-4
• 作为产物：
  描述：

  t-butyl 2-O-acetyl-4-fluoro-3,4-dideoxy-L-tetronate 在 三氟乙酸 作用下， 反应 4.0h， 生成 3,4-dideoxy-4-fluoro-L-glycero-tetronic acid
  参考文献：
  名称：

  Syntheses of fluorinated ligands to probe binding of antigenic determinants of Vibrio cholerae O:1, serotypes Inaba and Ogawa, to antibodies

  摘要：

  Derivatives of methyl alpha-glycosides of antigenic determinants of Vibrio cholerae O:1, serotypes Inaba and Ogawa, specifically Fluorinated at position 2' or 4' have been synthesized by coupling the appropriately fluorinated derivatives of 3-deoxy-L-glycero-tetronic acid with the methyl oc-glycosides of perosamine. The compound having the fluorine atom at position 2 was obtained by electrophilic addition of fluorine to the glycal derived from the parent antigenic determinant, serotypes Inaba, using Selectfluor(TM) as a fluorination reagent. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00505-4