(SS,2R,3R,4R)-2-tert-butanesulfinamido-3,4-(O-isopropylidene)-6-trimethylsilyl-1,1-difluoro-1-phenylselanyl-hex-5-yne | 1359718-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (SS,2R,3R,4R)-2-tert-butanesulfinamido-3,4-(O-isopropylidene)-6-trimethylsilyl-1,1-difluoro-1-phenylselanyl-hex-5-yne
• CAS: 1359718-17-4
• 化学式: C₂₂H₃₃F₂NO₃SSeSi
• 分子量: 536.617
• InChiKey: LNIVOKQJSGPLNA-YNGDTIAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (SS,2R,3R,4R)-2-tert-butanesulfinamido-3,4-(O-isopropylidene)-6-trimethylsilyl-1,1-difluoro-1-phenylselanyl-hex-5-yne 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 3.0h， 以86%的产率得到(S)-N-((2R,3R,4R)-1,1-difluoro-3,4-dihydroxy-1-(phenylselanyl)-6-(trimethylsilyl)hex-5-yn-2-yl)-2-methylpropane-2-sulfinamide
  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
• 作为产物：
  描述：

  [(4R,5R)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol 在 titanium(IV) tetraethanolate 、 四丁基氟化铵 、 四丁基二氟三苯硅酸铵 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 (SS,2R,3R,4R)-2-tert-butanesulfinamido-3,4-(O-isopropylidene)-6-trimethylsilyl-1,1-difluoro-1-phenylselanyl-hex-5-yne
  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