p-nitrophenyl 2,3,5-tri-O-acetyl-α-L-arabinofuranoside | 535960-64-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 2,3,5-tri-O-acetyl-α-L-arabinofuranoside
• 英文别名: 4-nitrophenyl 2,3,6-tri-O-acetyl-5-deoxy-α-L-arabino-hexofuranoside；[(2S,3S,4R,5S)-3,4-diacetyloxy-5-(4-nitrophenoxy)oxolan-2-yl]methyl acetate
• CAS: 535960-64-6
• 化学式: C₁₇H₁₉NO₁₀
• 分子量: 397.339
• InChiKey: ZBVZNCSOEDSIHI-MWDXBVQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 2,3,5-tri-O-acetyl-α-L-arabinofuranoside 在 4-二甲氨基吡啶 、 Lipolyve CC 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 phosphate buffer 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 4-nitrophenyl 5-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：

  p-nitrophenyl 2,5-di-O-acetyl-α-L-arabinofuranoside 在 吡啶 、 Candida cylindracea lipase 、 phosphate buffer 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 p-nitrophenyl 2,3,5-tri-O-acetyl-α-L-arabinofuranoside
  参考文献：
  名称：

  对硝基苯基α-L-阿拉伯呋喃糖苷的乙酸盐-通过脂肪酶的作用进行区域选择性制备。

  摘要：

  对-硝基苯基α-L-阿拉伯呋喃糖苷的所有可能的二-O-乙酸盐和单-O-乙酸盐是通过使用脂肪酶的化学酶法制备的。2,3-二-O-乙酸盐可以90％的收率通过将C-indylylylracerace脂肪酶（CCL）或ruged rugosa脂肪酶（LAY）的过-O-乙酰化对硝基苯基α-L-阿拉伯呋喃糖苷的伯乙酰基脱乙酰化而获得）。在有机溶剂中，通过洋葱假单胞菌脂肪酶（LPS-30）对对硝基苯基α-L-阿拉伯呋喃糖苷进行乙酰化，可得到2,5-和3,5-二-O-乙酸酯。通过猪胰脂肪酶催化的对硝基苯基α-L-阿拉伯呋喃糖苷的乙酰化，以95％的产率区域选择性地合成5-O-乙酸盐。最后，分两步获得对硝基苯基α-L-阿拉伯呋喃糖苷的2-和3-O-乙酸盐。

  DOI：

  10.1016/j.bmc.2005.10.023

文献信息

• Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases
  作者：Andrea Bordoni、Rosa M. de Lederkremer、Carla Marino

  DOI：10.1016/j.bmc.2010.05.038

  日期：2010.7

  Derivatives of 5-deoxy-beta-D-galactofuranose (5-deoxy-alpha-L-arabino-hexofuranose) have been synthesized starting from D-galacturonic acid. The synthesis of methyl 5-deoxy-alpha-L-arabino-hexofuranoside (14 alpha) was achieved by an efficient strategy previously optimized, involving a photoinduced electron transfer (PET) deoxygenation. Compound 14 alpha was converted into per-O-acetyl-5-deoxy-alpha,beta-L-arabino-hexofuranoside (16), an activated precursor for glycosylation reactions. The SnCl4-promoted glycosylation of 16 led to 4-nitrophenyl (19 alpha), and 4-methylthiophenyl 5-deoxy-alpha-L-arabino-hexofuranosides (20 alpha). The oxygenated analog 4-methylphenyl 1-thio-beta-D-galactofuranoside (23 beta) was also prepared. The 5-deoxy galactofuranosides were evaluated as inhibitors or substrates of the exo-beta-D-galactofuranosidase from Penicillium fellutanum, showing that the absence of HO-5 drastically diminishes the affinity for the protein. (C) 2010 Elsevier Ltd. All rights reserved.