(SS,2R,3R,4R)-2-tert-butanesulfinamido-1,1-difluoro-5-methylenecyclopentane-3,4-diol | 1359718-23-2

• 分子结构分类: 有机化合物 - 有机硫化合物
• 英文名称: (SS,2R,3R,4R)-2-tert-butanesulfinamido-1,1-difluoro-5-methylenecyclopentane-3,4-diol
• CAS: 1359718-23-2
• 化学式: C₁₀H₁₇F₂NO₃S
• 分子量: 269.313
• InChiKey: AUVRQAFUHVLVAK-OYNUMJSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.33
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  69.56
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 在 titanium(IV) tetraethanolate 、 偶氮二异丁腈 、 三正丁基氢锡 、 potassium carbonate 、 四丁基二氟三苯硅酸铵 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 8.75h， 生成 (SS,2R,3R,4R)-2-tert-butanesulfinamido-1,1-difluoro-5-methylenecyclopentane-3,4-diol
  参考文献：
  名称：

  Synthesis of exo-methylenedifluorocyclopentanes as precursors of fluorinated carbasugars by 5-exo-dig radical cyclization

  摘要：

  The synthesis of polyhydroxylated 1,1-difluoro-5-methylenecyclopentanes is described. The sequence involves an addition of PhSeCF2TMS to a tartrate-derived aldehyde or its corresponding tert-butanesulfinylimines followed by a radical cyclization. The use of a benzyl protected substrate led to an unproductive 1,5-hydrogen transfer after cyclization but the desired compound was eventually obtained from the unprotected substrate. A hydroboration/oxidation sequence was investigated on these 1,1-difluoro-5-methylenecyclopentanes as it would provide fluorinated carbasugars, a new and promising class of glycomimetics. Unfortunately, this reaction was poorly efficient and its regioselectivity not the expected one. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.02.015