methyl 4,6-dideoxy-4-(2,3-dideoxy-2-fluoro-L-glycero-tetronamido)-2-O-methyl-α-D-mannopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,6-dideoxy-4-(2,3-dideoxy-2-fluoro-L-glycero-tetronamido)-2-O-methyl-α-D-mannopyranoside
• 英文别名: methyl 4-(2,3-dideoxy-2-fluoro-D-glycero-tetronamido)-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside；(2R)-2-fluoro-4-hydroxy-N-[(2R,3S,4S,5S,6S)-4-hydroxy-5,6-dimethoxy-2-methyloxan-3-yl]butanamide
• 化学式: C₁₂H₂₂FNO₆
• 分子量: 295.308
• InChiKey: ATMRNRIODFHQDV-DZXYHILESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-氟二氢呋喃-2(3H)-酮 、 methyl 4-amino-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside 在 吡啶 作用下， 反应 6.0h， 以39.7%的产率得到methyl 4-(2,3-dideoxy-2-fluoro-L-glycero-tetronamido)-4,6-dideoxy-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