1,2,3,4,5-penta-O-acetyl-α-D-glucofuranose | 72002-47-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3,4,5-penta-O-acetyl-α-D-glucofuranose
• 英文别名: 1,2,3,5,6-Penta-O-acetyl-α-D-glucofuranose；[(2R)-2-acetyloxy-2-[(2R,3S,4R,5R)-3,4,5-triacetyloxyoxolan-2-yl]ethyl] acetate
• CAS: 72002-47-2
• 化学式: C₁₆H₂₂O₁₁
• 分子量: 390.344
• InChiKey: JRZQXPYZEBBLPJ-LJIZCISZSA-N

物化性质

• 沸点：
  460.3±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3,5,6-tri-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 在 三氟乙酸 作用下， 以 吡啶 、 水 为溶剂， 反应 7.5h， 生成 1,2,3,4,5-penta-O-acetyl-α-D-glucofuranose
  参考文献：
  名称：

  乙醛呋喃糖五乙酸酯的制备及性能

  摘要：

  与（1）H和（13）C NMR数据一起描述了醛糖醛呋喃糖五乙酸酯的16个对映体对中的每一个的一个异构体的制备。已获得八种异构体的结晶。已确定端基异构对的平衡值。

  DOI：

  10.1016/j.carres.2011.09.009

文献信息

• Practical synthesis of latent disarmed S-2-(2-propylthio)benzyl glycosides for interrupted Pummerer reaction mediated glycosylation
  作者：Yang Xu、Qian Zhang、Ying Xiao、Pinru Wu、Wei Chen、Zejin Song、Xiong Xiao、Lingkui Meng、Jing Zeng、Qian Wan

  DOI：10.1016/j.tetlet.2017.05.014

  日期：2017.6

  Practical synthetic methods to latent disarmed S-2-(2-propylthio)benzyl (SPTB) glycosides for interrupted Pummerer reaction mediated glycosylation have been discovered. Among them, both coupling reaction of PTB-Cl with glycosyl thiols and BF3·OEt2 promoted reaction of peracylated glycosides with PTB-SH produced peracylated SPTB glycosides in large scales and with high efficiency.

  已经发现了潜在的解除武装的S -2-（2-丙硫基）苄基（SPTB）糖苷用于中断的Pummerer反应介导的糖基化的实用合成方法。其中，PTB-Cl与糖基硫醇的偶联反应和BF 3 ·OEt 2均促进了过酰化的糖苷与PTB-SH的反应，从而大规模，高效地生产了过酰化的SPTB糖苷。
• The influence of boric acid on the acetylation of aldoses: ‘one-pot’ syntheses of penta-O-acetyl-β-D-glucofuranose and its crystalline propanoyl analogue
  作者：Richard H. Furneaux、Phillip M. Rendle、Ian M. Sims

  DOI：10.1039/b002841j

  日期：——

  When glucose and boric acid are heated in acetic acid a soluble compound forms from which, with acetic anhydride and catalytic amounts of sulfuric acid, a mixture consisting of >90% of the glucofuranose per-acetates (α∶β ratio 1∶1.8) is obtained in high yield. In the absence of the sulfuric acid partial acetylation takes place and penta-O-acetyl-β-D-glucofuranose (α∶β ratio 1∶52) is obtainable in good yield by removal of boric acid and completion of the esterification by addition of acetic anhydride and pyridine. A new, crystalline glucofuranose, penta-O-propanoyl-β-D-glucofuranose, is obtained in 58% yield in a ‘one-pot’ procedure using boric acid. The effects of boric acid on the acid-catalysed acetylation of other aldo-hexoses and -pentoses suggest that the synthesis of furanosyl per-esters could be successful with xylose and idose as well as with glucose. p

  当葡萄糖和硼酸在醋酸中加热时，会形成一种可溶性化合物，从中通过醋酐和少量的硫酸催化，可以获得含有>90%的葡萄呋喃糖全乙酸酯（α∶β比率为1∶1.8）的高产率混合物。在没有硫酸的情况下，会发生部分乙酰化，通过去除硼酸并加入醋酐和吡啶完成酯化反应，可以以良好的产率获得五-O-乙酰基-β-D-葡萄呋喃糖（α∶β比率为1∶52）。通过使用硼酸的“一锅法”程序，可以以58%的产率获得一种新的结晶葡萄呋喃糖，即五-O-丙酸酰基-β-D-葡萄呋喃糖。 硼酸对其他己醛糖和戊醛糖的酸催化乙酰化反应的影响表明，与葡萄糖一样，木糖和艾杜糖的呋喃糖全酯合成也可能是成功的。
• Per-O-acetylation of sugars catalysed by montmorillonite K-10
  作者：Pallooru Muni Bhaskar、Duraikkannu Loganathan

  DOI：10.1016/s0040-4039(98)00178-6

  日期：1998.4

  The inexpensive solid acid montmorillonite K-10, is shown to be an efficient catalyst for the per-O-acetylation of several mono-, di- and trisaccharides. The pyranose forms accounted for 75-100% of the acetylated products. (C) 1998 Elsevier Science Ltd. Ail rights reserved.
• H-Beta Zeolite as an Efficient Catalyst for Per-O-acetylation of Mono- and Disaccharides
  作者：Pallooru Muni Bhaskar

  DOI：10.1055/s-1999-2547

  日期：1999.1
• Sulfuric acid-catalyzed acetolysis of anomeric ethyl 2,3,4,6-tetra-O-acetyl-d-glucopyranosides: kinetics and mechanism
  作者：Józef Kaczmarek、Magda Preyss、Harri Lönnberg、Janusz Szafranek

  DOI：10.1016/0008-6215(95)00271-5

  日期：1995.12

  Kinetics of the acetolysis and concomitant anomerization of ethyl 2,3,4,6-tetra-O-acetyl-alpha- and -beta-D-glucopyranosides in a mixture of acetic anhydride, acetic acid, and sulfuric acid have been studied. The progress of the reactions was followed by gas chromatography, and the rate constants of the partial reactions were calculated on the basis of the time-dependent product distributions obtained. The mechanisms of the reactions are discussed.