4-O-(4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetylα-D-glucopyranosyl)-2,3,6-tri-O-acetyl-α/β-D-glucopyranosyl trichloroacetimidate | 250330-63-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-(4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetylα-D-glucopyranosyl)-2,3,6-tri-O-acetyl-α/β-D-glucopyranosyl trichloroacetimidate
• 英文别名: 4-O-(2,3,4,6-tetra-O-α-D-glucopyranosyl)-4-O-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl trichloroacetimidate；Glc2Ac3Ac4Ac6Ac(a1-4)Glc2Ac3Ac6Ac(a1-4)Glc2Ac3Ac6Ac-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-[(2R,3R,4S,5R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxy-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 250330-63-3
• 化学式: C₄₀H₅₂Cl₃NO₂₆
• 分子量: 1069.2
• InChiKey: UHZSSMWBPZCUTD-SDXQFPRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  70
• 可旋转键数：
  29
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  342
• 氢给体数：
  1
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  4-O-(4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetylα-D-glucopyranosyl)-2,3,6-tri-O-acetyl-α/β-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 potassium tert-butylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-(4-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of heparin-like antithrombotics having perphosphorylated thrombin binding domains

  摘要：

  The synthesis of three heparin analogues (i.e. compounds VI-VIII) having perphosphorylated thrombin binding domains (TBDs) is reported. These compounds were tested in vitro for their antithrombin III (ATIII)-mediated anti-Xa and antithrombin activities. Conjugates VI and VIII show a remarkable increase in antithrombin activity compared to the structurally related conjugates with persulfated TBDs (i.e. compounds IV and V), whereas compound VII displays a diminished activity.

  DOI：

  10.1016/s0968-0896(99)00139-x
• 作为产物：
  描述：

  maltotriose peracetate 在 乙酸肼 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 4-O-(4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetylα-D-glucopyranosyl)-2,3,6-tri-O-acetyl-α/β-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of heparin-like antithrombotics having perphosphorylated thrombin binding domains

  摘要：

  The synthesis of three heparin analogues (i.e. compounds VI-VIII) having perphosphorylated thrombin binding domains (TBDs) is reported. These compounds were tested in vitro for their antithrombin III (ATIII)-mediated anti-Xa and antithrombin activities. Conjugates VI and VIII show a remarkable increase in antithrombin activity compared to the structurally related conjugates with persulfated TBDs (i.e. compounds IV and V), whereas compound VII displays a diminished activity.

  DOI：

  10.1016/s0968-0896(99)00139-x

文献信息

• Alkylated resveratrol prodrugs and metabolites as potential therapeutics for neurodegenerative diseases
  作者：Pablo Peñalver、Efres Belmonte-Reche、Norma Adán、Marta Caro、María Luisa Mateos-Martín、Mario Delgado、Elena González-Rey、Juan Carlos Morales

  DOI：10.1016/j.ejmech.2018.01.037

  日期：2018.2

  its low efficacy and bioavailability. Here, we have designed and synthesized alkylated resveratrol prodrugs combining structural modification to improve antioxidant and anti-inflammatory properties and the preparation of prodrugs to extend drug bioavailability. For comparison we also studied resveratrol prodrugs and alkylated resveratrol derivatives. Methylated and butylated resveratrol derivatives showed

  白藜芦醇是一种天然存在的1,2-二苯乙烯，作为治疗几种神经退行性疾病的结果已显示出令人鼓舞的结果。然而，由于其低功效和生物利用度，其应用受到限制。在这里，我们设计和合成了烷基化白藜芦醇前药，结合结构修饰以改善抗氧化和抗炎特性，并制备前药以延长药物的生物利用度。为了进行比较，我们还研究了白藜芦醇前药和烷基化白藜芦醇衍生物。甲基化和丁基化的白藜芦醇衍生物在体外显示出最好的神经保护和抗炎活性。这些衍生物的葡糖基和葡糖基酰基前药对斑马鱼胚胎的毒性较低。在对戊四氮挑战的斑马鱼进行神经保护检查时，它们能够恢复神经元损害，但程度要低于白藜芦醇。然而，3- O-（6' - O-辛酰基）-β- d-吡喃葡萄糖苷白藜芦醇（化合物8）的AChE活性恢复超过100％，而白藜芦醇仅高达92％。在亨廷顿氏病的3-硝基丙酸小鼠模型中，白藜芦醇衍生物8通过改善运动活动并防止体重减轻，延缓了发病并降低了HD症状的严重程度。
• Westerduin, Pieter; Basten, Jan E. M.; Broekhoven, Marc A., Angewandte Chemie, 1996, vol. 108, # 3, p. 339 - 342
  作者：Westerduin, Pieter、Basten, Jan E. M.、Broekhoven, Marc A.、Kimpe, Vera de、Kuijpers, Will H. A.、Boeckel, Constant A. A.

  DOI：——

  日期：——
• Synthesis of archaeal glycolipid adjuvants—what is the optimum number of sugars?
  作者：Dennis M. Whitfield、Eva E. Eichler、G. Dennis Sprott

  DOI：10.1016/j.carres.2008.06.021

  日期：2008.9

  As part of a programme to optimize the use of archaeal-lipid liposomes (archaeosomes) as vaccine adjuvants, we present the synthesis and immunological testing of an oligomeric series of mannose glycolipids (Manp(1-5)). To generate the parent archaeol alcohol precursor, the polar lipids extracted from the archaeon Halobacterium salinarum were hydrolyzed to remove polar head groups, and the archaeol so generated partitioned into diethyl ether. This alcohol was then iteratively glycosylated with the donor 2-O-acetyl-3,4,6-tri-O-benzyl-alpha/beta-D-mannopyranosyl trichloroacetimidate to yield alpha-Manp-(1-->2) oligomers. A starch-derived trimer was also synthesized as a control. To promote hydration and form stable archaeosomes, an archaeal anionic lipid archaetidylglycerol (AG) was included in a 4:1 molar ratio. Archaeosomes prepared from Manp(1-2)-AG were recovered at only 34-37%, whereas Manp(3-4)-AG recoveries were 72-77%. Lipid recovery following hydration of Manp(5)-AG archaeosomes declined to 34%, indicating an optimum of 3-4 Manp units for bilayer formation. The CD8(+) T cell response in mice immunized with Manp(3-5) archaeosomes containing ovalbumin was highest for Manp(4) and declined for Manp(3) and Manp(5), revealing an optimum length of four unbranched units. The starch-derived trimer was more active than the Manp oligomers, suggesting the involvement of either a general binding lectin on antigen-presenting cells with highest affinity for triglucose or multiple lectin receptors. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.
• ANTITHROMBOTIC COMPOUNDS
  申请人：N.V. Organon

  公开号：EP1087992B1

  公开（公告）日：2008-08-20