(2R,5R)-5-(1,1'-dibromoethylen-2-yl)-2-((4-fluorophenoxy)methyl)-3,4-(isopropyledenedioxy)tetrahydrofuran | 851387-30-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,5R)-5-(1,1'-dibromoethylen-2-yl)-2-((4-fluorophenoxy)methyl)-3,4-(isopropyledenedioxy)tetrahydrofuran
• CAS: 851387-30-9
• 化学式: C₁₆H₁₇Br₂FO₄
• 分子量: 452.115
• InChiKey: AYEQSTXKGWIUPO-RJZRQDKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,5R)-5-(1,1'-dibromoethylen-2-yl)-2-((4-fluorophenoxy)methyl)-3,4-(isopropyledenedioxy)tetrahydrofuran 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以77%的产率得到(3aS,4R,6R,6aR)-4-Ethynyl-6-(4-fluoro-phenoxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole
  参考文献：
  名称：

  Stereoselective synthesis of (2R,3S,4S,5R)-trans-3,4-dihydroxy-5-(4-fluorophenoxymethyl)-2-(1-N-hydroxyureidyl-3-butyn-4-yl)tetrahydrofuran and (2R,3S,4S,5R)-trans-5-ethynyl-2-(4-fluorophenoxymethyl)-3,4-O-isopropylidene tetrahydrofuran from mannose diacetonide

  摘要：

  Stereoselective synthesis of pharmaceutically interesting chiral tetrahydrofurans starting from mannose diacetonide is reported. A 1,4-diol system derived from mannose diacetonide, through a Mitsunobu reaction was stereo specifically cyclized to give chiral tetrahydrofurans. Both the C-1 and C-4 centers Of D-mannose are successfully exploited to install the requisite side chains. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.046
• 作为产物：
  描述：

  3,6-anhydro-1,2:4,5-di-O-isopropylidene-7-O-(4-fluorophenyl)-D-glycero-D-mannoheptitol 在 盐酸 、 sodium periodate 、 碳酸氢钠 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 39.25h， 生成 (2R,5R)-5-(1,1'-dibromoethylen-2-yl)-2-((4-fluorophenoxy)methyl)-3,4-(isopropyledenedioxy)tetrahydrofuran
  参考文献：
  名称：

  Stereoselective synthesis of (2R,3S,4S,5R)-trans-3,4-dihydroxy-5-(4-fluorophenoxymethyl)-2-(1-N-hydroxyureidyl-3-butyn-4-yl)tetrahydrofuran and (2R,3S,4S,5R)-trans-5-ethynyl-2-(4-fluorophenoxymethyl)-3,4-O-isopropylidene tetrahydrofuran from mannose diacetonide

  摘要：

  Stereoselective synthesis of pharmaceutically interesting chiral tetrahydrofurans starting from mannose diacetonide is reported. A 1,4-diol system derived from mannose diacetonide, through a Mitsunobu reaction was stereo specifically cyclized to give chiral tetrahydrofurans. Both the C-1 and C-4 centers Of D-mannose are successfully exploited to install the requisite side chains. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.046