3-O-苄基-2,5-二脱氧-2-氟呋喃戊糖 | 786710-10-9

• 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: 3-O-苄基-2,5-二脱氧-2-氟呋喃戊糖
• 中文别名: S-{(9R)-1-[(2R,3S,4R,5R)-5-(6-氨基-9H-嘌呤-9-基)-4-羟基-3-(磷羧基氧代)四氢呋喃-2-基]-3,5,9-三羟基-8,8-二甲基-3,5-二羟基-10,14-二羰基-2,4,6-三氧杂-11,15-二氮杂-3lambda~5~,5lambda~5~-二磷杂十七烷-17-基}戊-3,4-二烯硫酸酯(壬-
• 英文名称: (2S,3S,4R,5R)-4-Benzyloxy-3-fluoro-5-methyl-tetrahydro-furan-2-ol
• 英文别名: 3-O-Benzyl-2,5-dideoxy-2-fluoro-alpha-D-arabinofuranose；(2S,3S,4R,5R)-3-fluoro-5-methyl-4-phenylmethoxyoxolan-2-ol
• CAS: 786710-10-9
• 化学式: C₁₂H₁₅FO₃
• 分子量: 226.248
• InChiKey: ISXYWHUUAQNVSF-KLHWPWHYSA-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：

  3-O-苄基-2,5-二脱氧-2-氟呋喃戊糖 在 吡啶 、 sodium tetrahydroborate 、 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.67h， 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
• 作为产物：
  描述：

  methyl 2-O-acetyl-3-O-benzyl-5-deoxy-α-D-ribofuranoside 在 吡啶 、 盐酸 、 四丁基氟化铵 、 sodium methylate 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 73.25h， 生成 3-O-苄基-2,5-二脱氧-2-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.