tetra-O-acetyl-α-D-galactopyranosyl bromide | 529493-92-3

• 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: tetra-O-acetyl-α-D-galactopyranosyl bromide
• 英文别名: ,23,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide；2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate；Acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-bromo-tetrahydro-pyran-3-yl ester；(3,4,5-triacetyloxy-6-bromooxan-2-yl)methyl acetate
• CAS: 529493-92-3
• 化学式: C₁₄H₁₉BrO₉
• 分子量: 411.203
• InChiKey: CYAYKKUWALRRPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

安全信息

• 储存条件：
  存储条件：2-8°C，需密封保存并在干燥处存放。

制备方法与用途

2,3,4,6-四-O-乙酰基α-半乳糖吡喃糖溴化物是一种PROTAC连接子，属于烷基链类，可用来合成PROTAC分子。

反应信息

• 作为反应物：
  描述：

  tetra-O-acetyl-α-D-galactopyranosyl bromide 在 甲醇 、 sodium hydroxide 、 水 、 苄基三乙基溴化铵 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 生成 2-tert-4,6-dinitrophenyl β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of aryl d-gluco- and d-galacto-pyranosides and 1-O-acyl-d-gluco- and -d-gluco-pyranoses exploiting the mitsunobu reaction. Influence of the pKa of the acid on the stereoselectivity of the reaction

  摘要：

  Glycosides (alpha- and beta-D-glucosides and -D-galactosides) derived from three pesticides, 2-tert-butyl-2,4-dinitrophenol,2,6-dibromo-4-cyanophenol, and 5-(2,4-dichlorophenoxy)-2-nitrobenzoic acid, were synthesized from 2,3,4,6-tetra-O-chloroacetyl-D-gluco- and -D-galactopyranose by use of the Mitsunobu reaction. It was shown that selectivity for the beta-D anomer increases with the pK(a) of the acid component.

  DOI：

  10.1016/s0008-6215(00)90559-7
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 水 、 乙酸酐 、 三溴化磷 作用下， 以68%的产率得到tetra-O-acetyl-α-D-galactopyranosyl bromide
  参考文献：
  名称：

  A water-soluble cholesteryl-containing Tris-galactoside: synthesis, properties, and use in directing lipid-containing particles to the liver

  摘要：

  The synthesis of a trisgalactoside-terminated cholesterol derivative is described. Tris(galactosyloxymethyl)-aminomethane is coupled to cholesterol by using glycyl and succinyl as intermediate hydrophilic spacer moieties. The resulting cholesteryl ester dissolves easily in water, forming monodisperse micelles. When added to dispersions of liposomes or plasma lipoproteins in water, the substance becomes incorporated rapidly into these structures, causing an increase of their buoyant density. Liposomes or low-density lipoproteins, preloaded with the substance, are rapidly cleared from the circulation and taken up by the liver after intravenous injection in rats. This uptake is inhibited by N-acetylgalactosamine but not by N-acetylglucosamine, indicating the specificity of this process.

  DOI：

  10.1021/jm00376a014

文献信息

• [EN] QUINONE METHIDE ANALOG SIGNAL AMPLIFICATION<br/>[FR] AMPLIFICATION DU SIGNAL D'ANALOGUES DE QUINONEMÉTHIDES
  申请人：VENTANA MED SYST INC

  公开号：WO2015124703A1

  公开（公告）日：2015-08-27

  Disclosed herein are novel quinone methide analog precursors and embodiments of a method and a kit of using the same for detecting one or more targets in a biological sample. The method of detection comprises contacting the sample with a detection probe, then contacting the sample with a labeling conjugate that comprises an enzyme. The enzyme interacts with a quinone methide analog precursor comprising a detectable label, forming a reactive quinone methide analog, which binds to the biological sample proximally to or directly on the target. The detectable label is then detected. In some embodiments, multiple targets can be detected by multiple quinone methide analog precursors interacting with different enzymes without the need for an enzyme deactivation step.

  本文披露了一种新型的醌甲烯类似物前体，以及使用该前体的方法和套件的实施例，用于检测生物样本中的一个或多个靶标。检测方法包括将样本与检测探针接触，然后将样本与包含酶的标记共轭物接触。酶与包含可检测标记的醌甲烯类似物前体相互作用，形成具有可检测标记的反应性醌甲烯类似物，该类似物与生物样本中的靶标近距离或直接结合。然后检测可检测标记。在某些实施例中，通过多个醌甲烯类似物前体与不同酶相互作用，无需酶去活化步骤即可检测多个靶标。
• [EN] SPHINGOSINE KINASE INHIBITOR PRODRUGS<br/>[FR] PRO-MÉDICAMENTS INHIBITEURS DE LA SPHINGOSINE KINASE
  申请人：APOGEE BIOTECHNOLOGY CORP

  公开号：WO2010105183A1

  公开（公告）日：2010-09-16

  The invention relates to prodrugs of hydroxyl-substituted adamantane compounds, pharmaceutical compositions thereof, and methods for inhibiting sphingosine kinase and for treating or preventing hyperproliferative disease, inflammatory disease, or angiogenic disease

  这项发明涉及羟基取代的金刚烷化合物的前药，其药物组合物，以及抑制神经酰胺激酶并治疗或预防过度增殖性疾病、炎症性疾病或血管生成性疾病的方法。
• Glycosylated Carboranylporphyrins and Uses Thereof
  申请人：Miura Michiko

  公开号：US20080279781A1

  公开（公告）日：2008-11-13

  The present invention is directed to low toxicity boronated compounds and methods for their use in the treatment, visualization, and diagnosis of tumors. More specifically, the present invention is directed to low toxicity glycosylated carborane-containing 5,10,15,20-tetraphenylporphyrin compounds and methods for their use particularly in boron neutron capture therapy (BNCT) and photodynamic therapy (PDT) for the treatment of tumors of the brain, and head and neck. The invention is also directed to using these glycosylated carborane-containing tetraphenylporphyrin compounds in methods of tumor imaging and/or diagnosis such as MRI, SPECT, or PET.

  本发明涉及低毒性硼化合物及其在肿瘤治疗、可视化和诊断中的使用方法。更具体地说，本发明涉及低毒性糖基化的含有5,10,15,20-四苯基卟啉的碳硼烷化合物及其在硼中子俘获治疗（BNCT）和光动力疗法（PDT）中的使用方法，特别用于治疗脑部、头颈部肿瘤。该发明还涉及使用这些糖基化的碳硼烷化合物在肿瘤成像和/或诊断方法中的应用，如MRI、SPECT或PET。
• Natural agent for treatment of gastrointestinal toxicity, associated symptoms and ulcers
  申请人：Rao Madusudana Janaswamy

  公开号：US20070213281A1

  公开（公告）日：2007-09-13

  The present invention relates to identification of Oroxylum indicum , Indian medicinal plant as a rich source for flavanoid compounds. Mucoprotective and antigastric ulcer properties in the flavone class of compounds isolated therefrom have been identified along with a flavanoids mixture in substantial yields from hexane and acetone extracts. The hexane extract was fractionated, purified and the compounds identified as Oroxylin A, Chrysin and Baicalein. The acetone extract was purified and the compounds obtained identified as methoxy chrysin, Oroxyloside methyl ester and chrysin-7-O-methyl glycoside.

  本发明涉及将印度药用植物印度酸枝鉴定为一种丰富的类黄酮化合物来源。从中分离出的黄酮类化合物中已确定具有粘膜保护和抗胃溃疡特性，同时还从己烷和丙酮提取物中获得了大量的类黄酮混合物。己烷提取物经过分级、纯化，鉴定出的化合物为千里光素A、槲皮素和黄芩素。丙酮提取物经过纯化，获得的化合物被鉴定为甲氧基黄芩素、千里光苷甲酯和黄芩-7-O-甲基糖苷。
• Synthesis of α- and β-glycosides containing spin labels, as probes for studies of carbohydrate-protein interaction
  作者：Nike R. Plessas、Irwin J. Goldstein

  DOI：10.1016/s0008-6215(00)85246-5

  日期：1981.3

  -glycopyranosides. Nitroxide spin-labeled α- d -glycopyranosides, as well as a β-maltoside, were synthesized by standard methods. The synthesis is also described of 2-amino-2-deoxy- d -glucose and - d -galactose derivatives having a spin label at C-2, and of the spin-labeled compound 1-[4-(β- d -galactopyranosyloxy)phenyl]-3-(2,2,6,6-tetramethylpiperidin-1-oxyl-4-yl)-2-thiourea.

  摘要通过使过邻苄基-α-d-甘露糖基溴化物与2,2,6,6-四甲基-4-哌啶子醇反应，以高收率和高度立体选择性的方式合成了一氧化氮自旋标记的α-d-吡喃葡萄糖苷在Lemieux等人设计的溴离子催化条件下。氢解后，解封的中间体被氧化，得到所需的自旋标记的α-d-糖吡喃糖苷。用标准方法合成了一氧化氮自旋标记的α-d-糖吡喃糖苷以及β-麦芽糖苷。还描述了在C-2处具有自旋标记的2-氨基-2-脱氧-d-葡萄糖和-d-半乳糖衍生物以及自旋标记的化合物1- [4-（β-d-吡喃半乳糖基氧基）的合成。 ）苯基] -3-（2,2,6,6-四甲基哌啶-1-氧基-1-基）-2-硫脲。