p-nitrophenyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane)-α-L-arabinofuranoside | 535960-68-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane)-α-L-arabinofuranoside
• 英文别名: (6aS,8S,9R,9aR)-8-(4-nitrophenoxy)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-ol
• CAS: 535960-68-0
• 化学式: C₂₃H₃₉NO₈Si₂
• 分子量: 513.736
• InChiKey: AVVCARYHRGSWRS-GSPCLOLRSA-N

物化性质

• 沸点：
  535.3±50.0 °C(predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane)-α-L-arabinofuranoside 在 四氢吡咯 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 4-nitrophenyl 2-O-(E)-feruloyl-α-L-arabinofuranoside
  参考文献：
  名称：

  Two efficient ways to 2-O- and 5-O-feruloylated 4-nitrophenyl α-l-arabinofuranosides as substrates for differentiation of feruloyl esterases

  摘要：

  4-Nitrophenyl 2-O-(E)-feruloyl-alpha-L-arabinofuranoside 1 and 4-nitrophenyl 5-O-(E)-feruloyl-alpha-L-arabinofuranoside 2 have been synthesized by two different routes. Monoferuloylation was accomplished by a chemoenzymatic sequence employing a regioselective transesterification catalyzed by lipases. The feruloyl group was introduced to enzymatically prepared 2,3- and 3,5-diacetates of 4-nitrophenyl alpha-L-arabinofurano side by reaction with 4-O-acetylferuloyl chloride. Removal of the protecting acetyl groups yielded 1 and 2. An alternative chemical synthesis suitable for preparation of larger quantities of 1 and 2 also is presented. The new substrates represent convenient tools to differentiate feruloyl esterases on the basis of their substrate specificity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00038-8
• 作为产物：
  描述：

  4-硝基苯基-ALPHA-L-阿拉伯糖甙 、 1,3二氯-1,1,3,3-四异丙基二硅氧烷 在 吡啶 作用下， 反应 6.0h， 以85%的产率得到p-nitrophenyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane)-α-L-arabinofuranoside
  参考文献：
  名称：

  Two efficient ways to 2-O- and 5-O-feruloylated 4-nitrophenyl α-l-arabinofuranosides as substrates for differentiation of feruloyl esterases

  摘要：

  4-Nitrophenyl 2-O-(E)-feruloyl-alpha-L-arabinofuranoside 1 and 4-nitrophenyl 5-O-(E)-feruloyl-alpha-L-arabinofuranoside 2 have been synthesized by two different routes. Monoferuloylation was accomplished by a chemoenzymatic sequence employing a regioselective transesterification catalyzed by lipases. The feruloyl group was introduced to enzymatically prepared 2,3- and 3,5-diacetates of 4-nitrophenyl alpha-L-arabinofurano side by reaction with 4-O-acetylferuloyl chloride. Removal of the protecting acetyl groups yielded 1 and 2. An alternative chemical synthesis suitable for preparation of larger quantities of 1 and 2 also is presented. The new substrates represent convenient tools to differentiate feruloyl esterases on the basis of their substrate specificity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00038-8

文献信息

• Investigation of the specificity of an α-l-arabinofuranosidase using C-2 and C-5 modified α-l-arabinofuranosides
  作者：Gérald Lopez、Caroline Nugier-Chauvin、Caroline Rémond、Michael O’Donohue

  DOI：10.1016/j.carres.2007.06.001

  日期：2007.11

  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.
• Two efficient ways to 2-O- and 5-O-feruloylated 4-nitrophenyl α-l-arabinofuranosides as substrates for differentiation of feruloyl esterases
  作者：Mária Mastihubová、Jana Szemesová、Peter Biely

  DOI：10.1016/s0040-4039(03)00038-8

  日期：2003.2

  4-Nitrophenyl 2-O-(E)-feruloyl-alpha-L-arabinofuranoside 1 and 4-nitrophenyl 5-O-(E)-feruloyl-alpha-L-arabinofuranoside 2 have been synthesized by two different routes. Monoferuloylation was accomplished by a chemoenzymatic sequence employing a regioselective transesterification catalyzed by lipases. The feruloyl group was introduced to enzymatically prepared 2,3- and 3,5-diacetates of 4-nitrophenyl alpha-L-arabinofurano side by reaction with 4-O-acetylferuloyl chloride. Removal of the protecting acetyl groups yielded 1 and 2. An alternative chemical synthesis suitable for preparation of larger quantities of 1 and 2 also is presented. The new substrates represent convenient tools to differentiate feruloyl esterases on the basis of their substrate specificity. (C) 2003 Elsevier Science Ltd. All rights reserved.