4’-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2’,3’,6’-tri-Oacetyl-D-glucopyranose | 18464-08-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4’-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2’,3’,6’-tri-Oacetyl-D-glucopyranose
• 英文别名: 2,3,6-tri-O-acetyl-4-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside；4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranose；β-Maltose-heptaacetat; 2,3,6,2',3',4',6'-Hepta-O-acetyl-β-maltose；Glc2Ac3Ac4Ac6Ac(a1-4)b-Glc2Ac3Ac6Ac；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-hydroxy-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 18464-08-9；66073-13-0；71623-44-4；101981-29-7；109922-72-7；109922-73-8；132287-75-3；132287-76-4；132287-78-6；132303-63-0；134311-82-3；134333-39-4
• 化学式: C₂₆H₃₆O₁₈
• 分子量: 636.561
• InChiKey: QBBPOGFLHMTZQB-PCIRLDFKSA-N

物化性质

• 沸点：
  667.0±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  44
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  232
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  烯丙醇 、 4’-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2’,3’,6’-tri-Oacetyl-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以31%的产率得到allyl hepta-O-acetyl-maltoside
  参考文献：
  名称：

  OLIGOSACCHARIDE DERIVATIVE

  摘要：

  公开号：

  EP1589023B1
• 作为产物：
  描述：

  phenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 在 chloroamine-T 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 4’-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2’,3’,6’-tri-O-acetyl-D-glucopyranose 、 4’-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2’,3’,6’-tri-Oacetyl-D-glucopyranose
  参考文献：
  名称：

  Chloramine-T-mediated chemoselective hydrolysis of thioglycosides into glycosyl hemiacetals under neutral conditions

  摘要：

  A metal-free, mild, efficient and chemoselective hydrolysis of several thioalkylglycosides (1) into their corresponding 1-hydroxy sugars (2) using sodium N-chloro-p-toluenesulfonamide trihydrate (chloramine-T) without affecting other functional groups is reported. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2003.12.020

文献信息

• Hafnium(IV) triflate as a potent catalyst for selective 1-O-deacetylation of peracetylated saccharides
  作者：Rui Wang、Ji-Zong Chen、Xiu-An Zheng、Rui Kong、Shan-Shan Gong、Qi Sun

  DOI：10.1016/j.carres.2017.11.015

  日期：2018.1

  An efficient method for selective anomeric deacetylation of peracetylated mono-, di-, and trisaccharides has been developed by using 2 mol% Hf(OTf)4 as catalyst in acetonitrile. Employment of ultrasonic irradiation could significantly accelerate the reaction rate. Mechanistic study confirmed the hydrolysis nature of this reaction, and NMR experimental data suggested that multiple peracetylated saccharide

  通过使用2 mol％的Hf（OTf）4作为乙腈中的催化剂，已经开发出一种有效的方法，用于将过乙酰化的单糖，二糖和三糖选择性异头脱乙酰。超声辐射的使用可以显着加快反应速度。机理研究证实了该反应的水解性质，NMR实验数据表明，多个过乙酰化的糖分子可能主要通过异头乙酸酯与Hf（IV）阳离子连接，从而促进其特异性水解。
• Sequential Dy(OTf)₃-Catalyzed Solvent-Free Per-<i>O</i>-Acetylation and Regioselective Anomeric De-<i>O</i>-Acetylation of Carbohydrates
  作者：Yi-Ling Yan、Jiun-Rung Guo、Chien-Fu Liang

  DOI：10.1002/asia.201700867

  日期：2017.9.19

  regioselective anomeric de‐O‐acetylation of carbohydrates can be tuned by adjusting the reaction medium. In this study, the per‐O‐acetylation of unprotected sugars by using a near‐stoichiometric amount of acetic anhydride under solvent‐free conditions resulted in the exclusive formation of acetylated saccharides as anomeric mixtures, whereas anomeric de‐O‐acetylation in methanol resulted in a moderate‐to‐excellent

  镝（III）三氟甲磺酸催化的per- ö -acetylation和区域选择性的端基异构脱ö碳水化合物-acetylation可以通过调节反应介质进行调谐。在这项研究中，在无溶剂条件下，通过使用接近化学计量的乙酸酐对未保护的糖进行过O-乙酰化，导致乙酰化糖类作为异头混合物独家形成，而异头De- O在甲醇中进行乙酰化可产生中等至优异的收率。与各种未保护的单糖或二糖的反应，然后半单步顺序转化为相应的乙酰化糖基半缩醛，也可导致高收率。此外，在Dy（OTf）3催化的糖基化反应后，获得的半缩醛可以成功转化为三氯亚氨酸盐。
• Synthesis of fluorinated maltose derivatives for monitoring protein interaction by ¹⁹F NMR
  作者：Michaela Braitsch、Hanspeter Kählig、Georg Kontaxis、Michael Fischer、Toshinari Kawada、Robert Konrat、Walther Schmid

  DOI：10.3762/bjoc.8.51

  日期：——

  A novel reporter system, which is applicable to the ¹⁹F NMR investigation of protein interactions, is presented. This approach uses 2-F-labeled maltose as a spy ligand to indirectly probe protein–ligand or protein–protein interactions of proteins fused or tagged to the maltose-binding protein (MBP). The key feature is the simultaneous NMR observation of both ¹⁹F NMR signals of gluco/manno-type-2-F-maltose-isomers; one isomer (α-gluco-type) binds to MBP and senses the protein interaction, and the nonbinding isomers (β-gluco- and/or α/β-manno-type) are utilized as internal references. Moreover, this reporter system was used for relative affinity studies of fluorinated and nonfluorinated carbohydrates to the maltose-binding protein, which were found to be in perfect agreement with published X-ray data. The results of the NMR competition experiments together with the established correlation between ¹⁹F chemical shift data and molecular interaction patterns, suggest valuable applications for studies of protein–ligand interaction interfaces.

  介绍了一种新的报告系统，适用于蛋白质相互作用的¹⁹F NMR研究。该方法使用2-F-标记的麦芽糖作为间谍配体，间接探测与融合或标记到麦芽糖结合蛋白（MBP）的蛋白质的蛋白质-配体或蛋白质-蛋白质相互作用。关键特征是同时观察α-葡萄糖型-2-F-麦芽糖异构体的¹⁹F NMR信号；一种异构体（α-葡萄糖型）结合到MBP并感知蛋白质相互作用，而非结合的异构体（β-葡萄糖型和/或α/β-甘露糖型）被用作内部参考。此外，该报告系统用于研究氟化和非氟化碳水化合物与麦芽糖结合蛋白的相对亲和力，发现与已发表的X射线数据完全一致。¹⁹F化学位移数据与分子相互作用模式之间的建立的相关性，以及NMR竞争实验的结果，提示了该系统在研究蛋白质-配体相互作用界面方面的有价值应用。
• A highly stereocontrolled synthesis of 1β,1β-linked acetylated oligosaccharides via orthoester formation-rearrangement
  作者：Wei Wang、Fanzuo Kong

  DOI：10.1016/s0040-4039(98)02626-4

  日期：1999.2

  1β,1β-Linked acetylated di-, tri-, and tetrasaccharides were synthesized in satisfactory yields and good stereoselectivities by a new method-orthoester formation and rearrangement under mild conditions.

  通过一种新方法-原酸酯的形成和在温和条件下的重排，以令人满意的产率和良好的立体选择性合成了1β，1β连接的乙酰化二糖，三糖和四糖。
• Preparation of 2,3,6,2′,3′,4′,6′-hepta-O-acetyl-maltose/cellobiose by enzymatic hydrolysis of maltose/cellobiose octaacetate
  作者：Geok-Toh Ong、Kung-Yao Chang、Shih-Hsiung Wu、Kung-Tsung Wang

  DOI：10.1016/0008-6215(94)00237-1

  日期：1994.12

  Partially protected monosaccharides with free anomeric hydroxyl groups are useful in the synthesis of oligosaccharides [ l-31. A number of chemical methods are reported to remove the anomeric acyl group of peracylated carbohydrates [ 4-61, providing a useful route to partially protected saccharides [ 7,8]. Enzymatic reactions have also been used for this purpose [ 9-231. According to previous reports

  具有游离异头羟基的部分保护的单糖可用于寡糖[1-31]的合成​​。据报道，有许多化学方法可以去除过酰化碳水化合物的异头酰基[4-61]，为部分保护糖类提供有用的途径[7,8]。酶促反应也已用于此目的[9-231。根据以前的报道，过乙酰化蔗糖中的伯乙酰酯是酶促水解的最活泼的位点[19-221，而过酰化的单糖（包括呋喃糖和吡喃糖）的异头位置是最活泼的位点[231. Fink和Hay报告说用低区域选择性的麦芽脂肪酶水解麦芽糖和纤维二糖八乙酸酯（1和2），得到了产物的混合物[91.在我们的工作中，化合物1和2仅在异头异构体位置被各种水解酶水解。检查了十多种酶对1和2的水解；结果列于表1和2。所有测试的酶均优先裂解异头酯（方案1）。在这些酶中，脂肪酶AP-6对两种底物的水解速率最高；蛋白酶II，蛋白酶N和脂肪酶N的发生率中等；脂肪酶P，脂肪酶AK，脂肪酶GC和脂肪酶CE的发生率很小。脂肪酶OF，脂肪