2-O-苄基-3,5-二脱氧-3-氟呋喃戊糖 | 786709-91-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-O-苄基-3,5-二脱氧-3-氟呋喃戊糖
• 中文别名: 2(3H)-噻唑亚胺,4-甲基-3-丙基-
• 英文名称: 2-O-Benzyl-3,5-dideoxy-3-fluoro-alpha-D-arabinofuranose
• 英文别名: (2S,3R,4R,5R)-4-fluoro-5-methyl-3-phenylmethoxyoxolan-2-ol
• CAS: 786709-91-9
• 化学式: C₁₂H₁₅FO₃
• 分子量: 226.248
• InChiKey: LVFFSWADXOTLLE-YJQGPUDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-O-苄基-3,5-二脱氧-3-氟呋喃戊糖 在 吡啶 、 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 草酰氯 、 sodium methylate 、 四氯化碲 、 对甲苯磺酸 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 7.67h， 生成 Phosphoric acid (2R,3S)-2-benzyloxy-3-fluoro-3-(2-methyl-[1,3]dioxan-2-yl)-propyl ester dimethyl ester
  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：

  1-O-methyl-3-deoxy-3-fluoro-α-D-arabinofuranose 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 三氟甲磺酸 、 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 环己烷 、 乙腈 为溶剂， 反应 8.5h， 生成 2-O-苄基-3,5-二脱氧-3-氟呋喃戊糖
  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

文献信息

• Study of 1-Deoxy-<scp>d</scp>-xylulose-5-phosphate Reductoisomerase:  Synthesis and Evaluation of Fluorinated Substrate Analogues
  作者：Alexander Wong、Jeffrey W. Munos、Vidusha Devasthali、Kenneth A. Johnson、Hung-wen Liu

  DOI：10.1021/ol048459b

  日期：2004.9.1

  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.