p-nitrophenyl 2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane)-α-L-arabinofuranoside | 953429-50-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-nitrophenyl 2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane)-α-L-arabinofuranoside
• CAS: 953429-50-0
• 化学式: C₂₃H₃₉NO₇Si₂
• 分子量: 497.736
• InChiKey: WQXLPIQQRUAUTO-XPWALMASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  89.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane)-α-L-arabinofuranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到p-nitrophenyl 2-deoxy-α-L-erythro-pentofuranoside
  参考文献：
  名称：

  Investigation of the specificity of an α-l-arabinofuranosidase using C-2 and C-5 modified α-l-arabinofuranosides

  摘要：

  The synthesis of three novel glycosyl donors presenting the same scaffold as alpha-L-arabinofuranose but modified at the C-2 or C-5 positions has been achieved. Furthermore, chemoenzymatic syntheses using the alpha-L-arabinofuranosidase AbfD3 and these unnatural furanosides were investigated. The use of the novel p-nitrophenyl furanoside donors revealed that AbfD3 can perform transglycosylation with the C-5 deoxygenated donor but not with the C-2 modified one. These results emphasize the vital role for OH-2 in AbfD3 substrate recognition. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.06.001
• 作为产物：
  描述：

  p-nitrophenyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane)-α-L-arabinofuranoside 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 生成 p-nitrophenyl 2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane)-α-L-arabinofuranoside
  参考文献：
  名称：

  Investigation of the specificity of an α-l-arabinofuranosidase using C-2 and C-5 modified α-l-arabinofuranosides

  摘要：

  The synthesis of three novel glycosyl donors presenting the same scaffold as alpha-L-arabinofuranose but modified at the C-2 or C-5 positions has been achieved. Furthermore, chemoenzymatic syntheses using the alpha-L-arabinofuranosidase AbfD3 and these unnatural furanosides were investigated. The use of the novel p-nitrophenyl furanoside donors revealed that AbfD3 can perform transglycosylation with the C-5 deoxygenated donor but not with the C-2 modified one. These results emphasize the vital role for OH-2 in AbfD3 substrate recognition. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.06.001