3-O-benzyl-1,4-dideoxy-4-fluoro-5-O-benzoyl-D-xylulose | 786710-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-O-benzyl-1,4-dideoxy-4-fluoro-5-O-benzoyl-D-xylulose
• CAS: 786710-13-2
• 化学式: C₁₉H₁₉FO₄
• 分子量: 330.356
• InChiKey: GTXJHVIGSPWQNI-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-1,4-dideoxy-4-fluoro-5-O-benzoyl-D-xylulose 在 2,6-二甲基吡啶 、 三甲基溴硅烷 、 sodium methylate 、 四氯化碲 、 对甲苯磺酸 作用下， 以 甲醇 、 氘代氯仿 、 二氯甲烷 、 苯 为溶剂， 反应 45.0h， 生成 1,4-dideoxy-4-fluoro-D-xylulose-5-phosphate
  参考文献：
  名称：

  Study of 1-Deoxy-d-xylulose-5-phosphate Reductoisomerase:  Synthesis and Evaluation of Fluorinated Substrate Analogues

  摘要：

  1-Deoxy-D-xylulose-5-phosphate (DXP) reductoisomerase is a NADPH-dependent enzyme catalyzing the conversion of DXP to methyl-D-erythritol 4-phosphate (MEP). In this study, each of the hydroxyl groups in DXP and one of its C-1 hydrogen atoms, were separately replaced with a fluorine atom and the effect of the substitution on the catalytic turnover was examined. It was found that the 1-fluoro-DXP is a poor substrate, while both 3- and 4-fluoro-DXP behave as noncompetitive inhibitors.

  DOI：

  10.1021/ol048459b
• 作为产物：
  描述：

  Trifluoro-methanesulfonic acid (2S,3R,4R,5R)-4-benzyloxy-2-methoxy-5-methyl-tetrahydro-furan-3-yl ester 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 草酰氯 、 四丁基氟化铵 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 73.67h， 生成 3-O-benzyl-1,4-dideoxy-4-fluoro-5-O-benzoyl-D-xylulose
  参考文献：
  名称：

  Study of 1-Deoxy-d-xylulose-5-phosphate Reductoisomerase:  Synthesis and Evaluation of Fluorinated Substrate Analogues

  摘要：

  1-Deoxy-D-xylulose-5-phosphate (DXP) reductoisomerase is a NADPH-dependent enzyme catalyzing the conversion of DXP to methyl-D-erythritol 4-phosphate (MEP). In this study, each of the hydroxyl groups in DXP and one of its C-1 hydrogen atoms, were separately replaced with a fluorine atom and the effect of the substitution on the catalytic turnover was examined. It was found that the 1-fluoro-DXP is a poor substrate, while both 3- and 4-fluoro-DXP behave as noncompetitive inhibitors.

  DOI：

  10.1021/ol048459b