tert-butyl [(2S,3S)-4,4-difluoro-2-[(2,2,2-trifluoroacetyl)amino]-1-trityloxyoctadecan-3-yl] carbonate | 1068564-86-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: tert-butyl [(2S,3S)-4,4-difluoro-2-[(2,2,2-trifluoroacetyl)amino]-1-trityloxyoctadecan-3-yl] carbonate
• CAS: 1068564-86-2
• 化学式: C₄₄H₅₈F₅NO₅
• 分子量: 775.94
• InChiKey: PVSOSUHIUWWCII-UWXQCODUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.5
• 重原子数：
  55
• 可旋转键数：
  26
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  在 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 反应 72.0h， 以20%的产率得到tert-butyl [(2S,3S)-4,4-difluoro-2-[(2,2,2-trifluoroacetyl)amino]-1-trityloxyoctadecan-3-yl] carbonate
  参考文献：
  名称：

  Synthesis and In Vivo Evaluation of 4-Deoxy-4,4-difluoro-KRN7000

  摘要：

  The synthesis of 4-deoxy-4,4-difluoro-KRN7000 starting from phytosphingosine is described. Key steps include a regioselective benzylation of azidophytosphingosine and a deoxofluor-mediated fluorination of the corresponding 4-ketone. This fluorination failed completely when the adjacent 3-OH was protected as benzyl ether but proceeded well when a benzoyl group was used. The biological evaluation reveals a bias toward Th1 cytokine induction upon Natural Killer T cell activation.

  DOI：

  10.1021/ol801663m

文献信息

• Synthesis and In Vivo Evaluation of 4-Deoxy-4,4-difluoro-KRN7000
  作者：Leo Leung、Cyrille Tomassi、Katrien Van Beneden、Tine Decruy、Dirk Elewaut、Tim Elliott、Aymen Al-Shamkhani、Christian Ottensmeier、Serge Van Calenbergh、Joern Werner、Tony Williams、Bruno Linclau

  DOI：10.1021/ol801663m

  日期：2008.10.16

  The synthesis of 4-deoxy-4,4-difluoro-KRN7000 starting from phytosphingosine is described. Key steps include a regioselective benzylation of azidophytosphingosine and a deoxofluor-mediated fluorination of the corresponding 4-ketone. This fluorination failed completely when the adjacent 3-OH was protected as benzyl ether but proceeded well when a benzoyl group was used. The biological evaluation reveals a bias toward Th1 cytokine induction upon Natural Killer T cell activation.