1,2,3,4,5-penta-O-acetyl-β-D-glucofuranose | 40031-23-0

• 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-β-D-glucofuranose
• 英文别名: 1,2,3,5,6-Penta-O-acetyl-β-D-glucofuranose；Penta-O-acetyl-β-D-glucofuranose；1,2,3,5,6-penta-O-acetyl-beta-D-glucofuranose；[(2R)-2-acetyloxy-2-[(2R,3S,4R,5S)-3,4,5-triacetyloxyoxolan-2-yl]ethyl] acetate
• CAS: 40031-23-0
• 化学式: C₁₆H₂₂O₁₁
• 分子量: 390.344
• InChiKey: JRZQXPYZEBBLPJ-IBEHDNSVSA-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

• 作为反应物：
  描述：

  1,2,3,4,5-penta-O-acetyl-β-D-glucofuranose 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 tetra-O-acetyl-ξ-D-glucofuranosyl chloride
  参考文献：
  名称：

  WO2006/55437

  摘要：

  公开号：
• 作为产物：
  描述：

  乙基 1-硫代-alpha-D-呋喃葡糖苷 在 mercury(II) diacetate 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 反应 3.5h， 生成 1,2,3,4,5-penta-O-acetyl-β-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。
• Antimicrobial agent
  申请人：Von Itzstein Mark Laurence

  公开号：US20050124559A1

  公开（公告）日：2005-06-09

  A compound of general formula (I): wherein R 1 and R 2 may be the same or different and are selected from the group consisting of hydrogen, optionally substituted C 4-30 alkyl and optionally substituted C 4-30 alkenyl, provided that R 1 and R 2 may not both be hydrogen, or R 1 and R 2 together with the nitrogen atom from which they depend form a saturated or unsaturated, optionally substituted heterocyclic group which may include additional heteroatoms selected from the group consisting of O, N and S, or R 1 and R 2 together with the nitrogen atom from which they depend form an optionally substituted lactam moiety; X 1 is selected from the group consisting of OR 3 , SR 3 , NR 3 R′ 3 , hydrogen, halogen, CN, C(O)NR 3 R′ 3 , C(O)OR 3 , OSO 3 R 3 , OPO 3 R 3 , NNR 3 R′ 3 , SNR 3 R′ 3 , NHSR 3 , SSR 3 and substituted alkyl; X 2 is selected from the group consisting of OR 4 , SR 4 , NR 4 R′ 4 , hydrogen, halogen, CN, C(O)NR 4 R′ 4 , C(O)OR 4 , OSO 3 R 4 , OPO 3 R 4 , NNR 4 R′ 4 , SNR 4 R′ 4 , NHSR 4 , SSR 4 and substituted alkyl; X 3 is selected from the group consisting of OR 5 , SR 5 , NR 5 R′ 5 , hydrogen, halogen, CN, C(O)NR 5 R′ 5 , C(O)OR 5 , OSO 3 R 5 , OPO 3 R 5 R′ 5 , NNR 5 R′ 5 , SNR 5 R′ 5 , NHSR 5 , SSR 5 and substituted alkyl; X 4 is selected from the group consisting of OR 6 , SR 6 , NR 6 R′ 6 , hydrogen, halogen, CN, C(O)NR 6 R′ 6 , C(O)OR 6 , OSO 3 R 6 , OPO 3 R 6 R′ 6 , NNR 6 R′ 6 , SNR 6 R′ 6 , NHSR 6 , SSR 6 and substituted alkyl; R 3 , R′ 3 , R 4 , R′ 4 , R 5 , R′ 5 , R 6 and R′ 6 are the same or different and are selected from the group consisting of hydrogen, optionally substituted alkyl, optionally substituted aralkyl, optionally substituted aryl, optionally substituted acyl and a carbohydrate moiety; or a pharmaceutically acceptable salt thereof.

  通式（I）的化合物：其中R1和R2可以相同或不同，并且从氢，可选取代的C4-30烷基和可选取代的C4-30烯基的群中选择，前提是R1和R2不能同时为氢，或者R1和R2与它们所依赖的氮原子一起形成饱和或不饱和的、可选取代的杂环基团，该基团可以包括从O、N和S的群中选择的额外杂原子，或者R1和R2与它们所依赖的氮原子一起形成可选取代的内酰胺基团；X1从OR3、SR3、NR3R′3、氢、卤素、CN、C（O）NR3R′3、C（O）OR3、OSO3R3、OPO3R3、NNR3R′3、SNR3R′3、NHSR3、SSR3和取代烷基的群中选择；X2从OR4、SR4、NR4R′4、氢、卤素、CN、C（O）NR4R′4、C（O）OR4、OSO3R4、OPO3R4、NNR4R′4、SNR4R′4、NHSR4、SSR4和取代烷基的群中选择；X3从OR5、SR5、NR5R′5、氢、卤素、CN、C（O）NR5R′5、C（O）OR5、OSO3R5、OPO3R5R′5、NNR5R′5、SNR5R′5、NHSR5、SSR5和取代烷基的群中选择；X4从OR6、SR6、NR6R′6、氢、卤素、CN、C（O）NR6R′6、C（O）OR6、OSO3R6、OPO3R6R′6、NNR6R′6、SNR6R′6、NHSR6、SSR6和取代烷基的群中选择；R3、R′3、R4、R′4、R5、R′5、R6和R′6可以相同或不同，并且从氢、可选取代的烷基、可选取代的芳基烷基、可选取代的芳基、可选取代的酰基和碳水化合物基团中选择；或其药学上可接受的盐。
• 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