6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate | 154970-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: [(2R,3S,4R,5R,6R)-5-azido-3,4-bis(phenylmethoxy)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate
• CAS: 154970-28-2
• 化学式: C₂₄H₂₅Cl₃N₄O₆
• 分子量: 571.845
• InChiKey: ZLPSPCBQPLCOIH-ZGJYDULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate 在 chromium(VI) oxide 、 硫酸 、 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 15.5h， 生成 allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-2-O-acetyl-3-O-benzyl-α-L-idopyranosiduronate
  参考文献：
  名称：

  Synthesis of disaccharidic sub-units of a new series of heparin related oligosaccharides

  摘要：

  The chemical synthesis of disaccharides 1 and 2, useful building-blocks for the preparation of a new series of heparin related oligosaccharides containing the unusual sequence (GlcN-IdoA)(n), is described. In addition, the orthogonality of the protective groups would allow access to a wide array of differently sulfated oligosaccharides. As the simplest members of this new class of oligomer, the synthesis of sulfated disaccharides 3 and 4 fully deprotected is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00526-8
• 作为产物：
  描述：

  thexyldimethylsilyl 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside 在 四丁基氟化铵 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 45.0h， 生成 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of disaccharidic sub-units of a new series of heparin related oligosaccharides

  摘要：

  The chemical synthesis of disaccharides 1 and 2, useful building-blocks for the preparation of a new series of heparin related oligosaccharides containing the unusual sequence (GlcN-IdoA)(n), is described. In addition, the orthogonality of the protective groups would allow access to a wide array of differently sulfated oligosaccharides. As the simplest members of this new class of oligomer, the synthesis of sulfated disaccharides 3 and 4 fully deprotected is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00526-8

文献信息

• [EN] OLIGOSACCHARIDE COMPOUNDS FOR USE IN MOBILISING STEM CELLS<br/>[FR] COMPOSÉS D'OLIGOSACCHARIDE POUR UTILISATION DANS LA MOBILISATION DE CELLULES SOUCHES
  申请人：ENDOTIS PHARMA

  公开号：WO2010029185A1

  公开（公告）日：2010-03-18

  A compound of the following formula or a salt, solvate or formula (I) and a pharmaceutical composition containing said compound. It concerns also its use in the treatment of cancer and/or of pathological angiogenesis and/or in promoting the mobilisation of stem cells, in particular hematopoietic stem cells.

  以下化学式的化合物或盐、溶剂化合物或化学式（I）以及含有该化合物的药物组合物。它还涉及其在治疗癌症和/或病理性血管生成和/或促进干细胞动员，特别是造血干细胞方面的用途。
• Solid- and solution-phase synthesis of heparin and other glycosaminoglycans
  申请人：——

  公开号：US20030013862A1

  公开（公告）日：2003-01-16

  Described is a modular, general synthetic strategy for the preparation in solution and on a solid support of heparin, heparin-like glycosaminoglycans, glycosaminoglycans and non-natural analogs of each of them. Additionally, the modular strategy provides the basis for the preparation of combinatorial libraries and parallel libraries of defined glycosaminoglycan oligosaccharides. The defined glycosaminoglycan structures may be used in high-throughput screening experiments to identify carbohydrate sequences that regulate a host of recognition and signal-transduction processes. The determination of specific sequences involved in receptor binding holds great promise for the development of molecular tools which will allow modulation of processes underlying viral entry, angiogenesis, kidney diseases and diseases of the central nervous system. Notably, the present invention enables the automated synthesis of glycosaminoglycans in much the same fashion that peptides and oligonucleotides are currently assembled.

  描述了一种模块化的通用合成策略，用于在溶液中和固体支撑上制备肝素、类肝素糖胺聚糖、糖胺聚糖以及它们的每一种非天然类似物。此外，该模块化策略为定义的糖胺聚糖寡糖的组合库和平行库的制备提供了基础。定义的糖胺聚糖结构可以用于高通量筛选实验，以识别调节多种识别和信号转导过程的碳水化合物序列。确定参与受体结合的特定序列对于开发分子工具具有巨大的前景，这些工具将允许调节病毒进入、血管生成、肾脏疾病和中枢神经系统疾病等过程。值得注意的是，本发明使得能够以目前组装肽和寡核苷酸的方式自动化合成糖胺聚糖。
• [EN] AN EFFICIENT AND SCALABLE PROCESS FOR THE MANUFACTURE OF FONDAPARINUX SODIUM<br/>[FR] PROCÉDÉ EFFICACE ET EXTENSIBLE DE FABRICATION DE FONDAPARINUX SODIQUE
  申请人：RELIABLE BIOPHARMACEUTICAL CORP

  公开号：WO2013115817A1

  公开（公告）日：2013-08-08

  The present invention relates to a process for the synthesis of the Factor Xa anticoagulent Fondaparinux and related compounds. The invention relates, in addition, to efficient and scalable processes for the synthesis of various intermediates useful in the synthesis of Fondaparinux and related compounds.

  本发明涉及一种用于合成因子Xa抗凝剂Fondaparinux及相关化合物的过程。此外，该发明还涉及用于合成Fondaparinux及相关化合物的各种中间体的高效可扩展过程。
• Synthesis of S-linked thiooligosaccharide analogues of Nod factors: synthesis of new protected thiodisaccharide and thiotrisaccharide intermediates
  作者：Latino Loureiro Morais、Khalil Bennis、Isabelle Ripoche、Liang Liao、France-Isabelle Auzanneau、Jacques Gelas

  DOI：10.1016/s0008-6215(03)00149-6

  日期：2003.6

  influence of our protecting group strategy, the glycosylation of 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-beta-D-glucopyranoside (7) with two trichloroacetimidate glycosyl donors carrying an azido group at C-2 and either benzyl or benzoyl protecting groups on O-3 and O-4 was first attempted under catalysis with BF(3).Et(2)O in toluene. While glycosylation with the benzoylated glycosyl donor gave only a poor

  我们正在研究结瘤因子的硫代类似物的合成，该结节因子对几丁质酶的降解具有抗性。为了研究我们保护基策略的影响，将1,6-脱水-2-叠氮基-3-O-苄基-2-脱氧-β-D-吡喃葡萄糖苷（7）与两个带有叠氮基的三氯乙酰亚氨酸糖基供体进行糖基化首先在BF（3）.Et（2）O的甲苯催化下，尝试在C-2上的C2和O-3和O-4上的苄基或苯甲酰基保护基团进行尝试。虽然用苯甲酰化的糖基供体进行糖基化仅产生较差的二糖（27％），但与苄基化的供体的类似反应以良好的收率（77％）给出了相应的二糖。尽管两种产物均以异头混合物形式获得，但苄基化的供体导致改善的立体选择性，有利于所需的β-端基异构体（α：β3：7）。基于这些结果，通过7与6-O-乙酰基-4-S-（3,4,6-三-O-乙酰基-2-苄氧基羰基氨基-2-脱氧-β-D的偶联反应合成了一种新型的硫代三糖还新合成了-（吡喃葡萄糖基）-2-叠氮基-3-O-苄基-2-
• Synthesis of new fluorescently labeled glycosylphosphatidylinositol (GPI) anchors
  作者：Varma Saikam、Riya Raghupathy、Mahipal Yadav、Veeranjaneyulu Gannedi、Parvinder Pal Singh、Naveed A. Qazi、Sanghapal D. Sawant、Ram A. Vishwakarma

  DOI：10.1016/j.tetlet.2011.06.005

  日期：2011.8

  The borondipyrromethene (BODIPY) labeled new glycosylphosphatidylinositol (GPI) molecules were synthesized as cellular probes to study the chemical basis of microdomain organization of GPI-anchored proteins and cholesterol in plasma membrane. The synthesis enabled by a new stereo-selective glycosylation of myo-d-inositol acceptor led to the preparation of optically pure glucosaminyl-(1-6)-α-phosph

  合成了硼联苯二甲亚甲基（BODIPY）标记的新糖基磷脂酰肌醇（GPI）分子作为细胞探针，研究了GPI锚定蛋白质和质膜中胆固醇的微区组织的化学基础。合成能够通过一个新的立体选择性糖基化肌醇- d肌醇受体导致光学纯glucosaminyl-（1-6）-α-磷脂酰的制备肌醇- d肌醇和其非天然立体异构体。