4-nitrophenyl 2,3-di-O-acetyl-β-D-xylopyranoside | 162088-88-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl 2,3-di-O-acetyl-β-D-xylopyranoside
• 英文别名: [(2S,3R,4S,5R)-3-acetyloxy-5-hydroxy-2-(4-nitrophenoxy)oxan-4-yl] acetate
• CAS: 162088-88-2
• 化学式: C₁₅H₁₇NO₉
• 分子量: 355.301
• InChiKey: NRWYACQCGLVVJG-BARDWOONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl 2,3-di-O-acetyl-β-D-xylopyranoside 在 3 A molecular sieve 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.75h， 生成 p-nitrophenyl β-D-xylopyranosyl-(1->4)-β-D-xylopyranoside
  参考文献：
  名称：

  β-木糖苷的短合成

  摘要：

  摘要苄基2,3,2'，3'，4'-戊-O-乙酰基-β-木糖苷，2-硝基苯基β-木糖苷，4-硝基苯基β-木糖苷和2-碘苄基1-硫代-β-木糖苷通过短而高度选择性的途径合成。使用二丁基氧化锡和三乙基甲硅烷基氯选择性地将β-d-吡喃吡喃糖苷4-O-三乙基甲硅烷基化，然后将2，3-二-O-乙酰化。在酸性条件下进行甲硅烷基化得到4-未保护的木糖苷，然后使用2,3,4-三-O-乙酰基-α-d-木吡喃糖基三氯乙酰亚氨酸酯将其β-d-木糖基化。

  DOI：

  10.1016/0008-6215(94)00214-2
• 作为产物：
  描述：

  tetra-O-acetyl-β-D-xylopyranose 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 水 、 乙酸酐 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 4-nitrophenyl 2,3-di-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  一种含有炔丙基的木糖及其合成方法

  摘要：

  本发明公开了一种含有炔丙基的木糖及其制备方法，该方法以D‑木糖为原料，将其进行全乙酰基保护，将得到的化合物的异头位引入对硝基苯氧基，然后脱除乙酰基得到化合物A；将得到的化合物A的2位或3位或4位上引入叔丁基二甲基，得到化合物B、化合物C和化合物D，并且将其分离；分别对化合物B、化合物C和化合物D的羟基进行乙酰基保护，然后脱除叔丁基二甲基，分别在2位、3位和4位上引入炔丙基，得到含有炔丙基的木糖。本发明所公开的方法通过使用叔丁基二甲基(TBS)占位的方法首次使炔丙基选择性的连接到木糖上，为此木糖后续连接到蛋白质或氨基酸提供了平台，为以后的生物学研究打下了基础。

  公开号：

  CN111423478A

文献信息

• Preparation of regioselectively feruloylated p-nitrophenyl α-l-arabinofuranosides and β-d-xylopyranosides—convenient substrates for study of feruloyl esterase specificity
  作者：Mária Mastihubová、Peter Biely

  DOI：10.1016/j.carres.2010.03.034

  日期：2010.6

  as deacetylation method. Under these conditions a significant feruloyl migration was observed mainly on p-nitrophenyl 3-O-feruloyl-beta-D-xylopyranoside resulting in low yields of the positional isomers. Investigation of substrate and positional specificity of different types of feruloyl esterases on the presented compounds in enzyme-coupled assays was reported previously.

  对-硝基苯基α-L-阿拉伯呋喃糖苷和β-D-吡喃吡喃糖苷单-O-阿魏酸酯是通过相应的酶促制备的二-O-乙酸酯的4-O-乙酰基阿魏酸酯化，然后进行脱乙酰化而制备的。在吡喃吡喃糖苷衍生物上测试了由氧化锌催化的另一种轻度酰化反应。使用中性催化剂二丁基氧化锡在回流下对乙酰基进行化学选择性甲醇分解作为脱乙酰基方法。在这些条件下，主要在对硝基苯基3-O-阿魏酰基-β-D-吡喃吡喃糖苷上观察到明显的阿魏酰基迁移，导致位置异构体的产率低。先前已经报道了在酶联测定中研究不同类型的阿魏酸酯酶对所提供化合物的底物和位置特异性的研究。
• Lipase-catalysed preparation of acetates of 4-nitrophenyl β-d-xylopyranoside and their use in kinetic studies of acetyl migration
  作者：Mária Mastihubová、Peter Biely

  DOI：10.1016/j.carres.2004.02.016

  日期：2004.5

  Di-O-acetates and mono-O-acetates of 4-nitrophenyl beta-D-xylopyranoside were prepared by use of lipase PS-30. Polarity of organic solvents and reaction time affected the regioselectivity of the di-O-acetylation as well as the yields of monoacetates. The kinetics of acetyl groups migration in these derivatives was studied in aqueous media using HPLC. Migration of the acetyl group strongly depended on pH. The highest rate of acetyl migration was observed from O-2 to O-3 in both 2,4-di-O-acetate and 2-O-acetate. On the contrary, acetyl exchange between O-3 and O-4 in both directions was slower than between O-2 and O-3. The 2,3-di-O-acetate and 4-O-acetate showed to be the most stable towards acetyl migration. The 3,4-di-O-acetate and 4-O-acetate were dominant in the corresponding equilibration mixtures. (C) 2004 Elsevier Ltd. All rights reserved.
• Regioselective monohydrolysis of per-O-acetylated-1-substituted-β-glucopyranosides catalyzed by immobilized lipases
  作者：Adriano A. Mendes、Dasciana S. Rodrigues、Marco Filice、Roberto Fernandez-Lafuente、Jose M. Guisan、Jose M. Palomo

  DOI：10.1016/j.tet.2008.08.099

  日期：2008.11

  The regioselective monohydrolysis of different peracetylated-beta-glucopyranosides in aqueous media using immobilized preparations of three different lipases-those from Aspergillus niger (ANL), Candida rugose (CRL) and Candida antarctica B (CAL-B)-has been Studied. Three very different immobilization strategies-covalent attachment, anionic exchange and interfacial activation oil a hydrophobic sopport-were employed for each lipase. The role of the immobilization strategy and the effect of the presence of different moieties in the anomeric position of the substrate on the hydrolytic activities, specificities and regioselectivities of the lipases were investigated. For example, the PEI-ANL preparation exhibited 800 times higher activity than the octyl-ANL in the hydrolysis of 2-acetamido-2-deoxy-1-(4-nitrophenyl)-3,4,6-tri-O-acetyl-beta-D-glucopyranoside-producing 4-OH derivative in 18% yield-whereas the octyl-ANL was five times more active than the PEI-ANL in the hydrolysis of 1-(4-nitrophenyl)-2,3,4-tri-O-acetyl-beta-D-xylopyranoside, producing 4-OH monohydroxy product in >99% yield.The octyl-CRL preparation hydrolyzed regioselectively 3,4,6-tri-O-acetyl-glucal in position 6 in 68% yield while the PEI-CRL produced the 3-OH product in 11% yield, although with moderate specificity. The CNBr-CAL-B hydrolyzed specifically and regioselectively the glucal producing the 3-OH product in >99% yield. (C) 2008 Elsevier Ltd. All rights reserved.
• Escherichia coli LacZ β-galactosidase inhibition by monohydroxy acetylated glycopyranosides: Role of the acetyl groups
  作者：Jana Brabcova、Cesar Carrasco-Lopez、Teodora Bavaro、Juan A. Hermoso、Jose M. Palomo

  DOI：10.1016/j.molcatb.2014.05.008

  日期：2014.9