O-(2-O-benzoyl-3,4,6-tri-O-benzyl-D-glucopyranosyl)trichloroacetimidate | 213681-58-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2-O-benzoyl-3,4,6-tri-O-benzyl-D-glucopyranosyl)trichloroacetimidate
• CAS: 213681-58-4
• 化学式: C₃₆H₃₄Cl₃NO₇
• 分子量: 699.027
• InChiKey: AHWNPSJPXORJSA-TUBWMVHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.69
• 重原子数：
  47.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  96.3
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  O-(2-O-benzoyl-3,4,6-tri-O-benzyl-D-glucopyranosyl)trichloroacetimidate 在 sodium hydroxide 、 4 Angstroem MS 、 三氟化硼乙醚 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 2,6-dimethoxyphenyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Total Synthesis of Vancomycin—Part 4: Attachment of the Sugar Moieties and Completion of the Synthesis

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19990903)5:9<2648::aid-chem2648>3.0.co;2-q
• 作为产物：
  描述：

  phenyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.0h， 生成 O-(2-O-benzoyl-3,4,6-tri-O-benzyl-D-glucopyranosyl)trichloroacetimidate
  参考文献：
  名称：

  Total Synthesis of Vancomycin—Part 4: Attachment of the Sugar Moieties and Completion of the Synthesis

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19990903)5:9<2648::aid-chem2648>3.0.co;2-q

文献信息

• β(1,3) Branched heptadeca- and linear hexadeca-saccharides possessing an aminoalkyl group as a strong ligand to dectin-1
  作者：Hiroshi Tanaka、Tetsuya Kawai、Yoshiyuki Adachi、Naohito Ohno、Takashi Takahashi

  DOI：10.1039/c0cc03153d

  日期：——

  In this report, we describe the convergent synthesis of β(1,3) oligosaccharides containing an aminoalkyl group. The branched heptadecasaccharide and linear hexadecasaccharide acted as ligands of dectin-1 whose binding affinity was only 10-fold weaker than that of natural SPG and exhibited dectin-1 agonist activity.

  在本报告中，我们描述了含有氨基烷基团的β(1,3)低聚糖的汇聚合成。分支的十七糖和线性的十六糖作为dectin-1的配体，其结合亲和力仅比天然SPG弱10倍，并展现出dectin-1激动剂活性。
• A One-Pot Synthesis of Glycans and Nucleosides Based on <i>ortho</i>-(1-Phenylvinyl)benzyl Glycosides
  作者：Rui Yang、Haiqing He、Zixi Chen、Yingying Huang、Guozhi Xiao

  DOI：10.1021/acs.orglett.1c02998

  日期：2021.11.5

  synthesis of both glycans and nucleosides remains rare and challenging. Herein, we report a one-pot glycosylation strategy for glycans and nucleosides synthesis based on ortho-(1-phenylvinyl)benzyl glycosides, which has several advantages, including no aglycon transfers, no undesired interference of departing species, no unpleasant odor, and up to the construction of four different glycosidic linkages

  聚糖和核苷的一锅法合成仍然很少见且具有挑战性。在此，我们报告了一种基于邻-(1-苯基乙烯基)苄基糖苷的聚糖和核苷合成的一锅糖基化策略，该策略具有几个优点，包括无糖苷配基转移、无离去物种的不良干扰、无难闻气味等。构建四种不同的糖苷键。
• An orthogonal and reactivity-based one-pot glycosylation strategy for both glycan and nucleoside synthesis: access to TMG-chitotriomycin, lipochitooligosaccharides and capuramycin
  作者：Haiqing He、Lili Xu、Roujing Sun、Yunqin Zhang、Yingying Huang、Zixi Chen、Penghua Li、Rui Yang、Guozhi Xiao

  DOI：10.1039/d0sc06815b

  日期：——

  (O-glycosides) and nucleosides (N-glycosides) play important roles in numerous biological processes. Chemical synthesis is a reliable and effective means to solve the attainability issues of these essential biomolecules. However, due to the stereo- and regiochemical issues during glycan assembly, together with problems including the poor solubility and nucleophilicity of nucleobases in nucleoside synthesis, the

  聚糖（ O-糖苷）和核苷（ N-糖苷）在许多生物过程中都发挥着重要作用。化学合成是解决这些重要生物分子的可获得性问题的可靠且有效的手段。然而，由于聚糖组装过程中的立体和区域化学问题，以及核苷合成中核碱基的溶解度和亲核性差等问题，高效合成聚糖和核苷的一锅糖基化策略的开发仍然很差且具有挑战性。在这里，我们报告了第一个基于糖基原-(1-苯基乙烯基)苯甲酸酯的正交和基于反应性的一锅糖基化策略，适用于聚糖和核苷合成。这种一锅糖基化策略不仅继承了先前开发的基于糖基原炔基苯甲酸酯的正交一锅糖基化策略的优点，包括无苷元转移、无离开物种的干扰、无难闻气味等优点，而且高度扩展了糖基化的应用范围。范围（聚糖和核苷）并增加可用于多步一锅合成的离去基团的数量（最多形成四个不同的糖苷键）。 特别是，目前的一锅法糖基化策略已成功应用于一种有前景的结核病药物主角卡普拉霉素的全合成，以及对β- N-乙酰氨基葡萄糖苷酶和重要
• Chemical Synthesis of Residue-Selectively ¹³C and ²H Double-Isotope-Labeled Oligosaccharides as Chemical Probes for the NMR-Based Conformational Analysis of Oligosaccharides
  作者：Hiroki Hamagami、Yoshiki Yamaguchi、Hiroshi Tanaka

  DOI：10.1021/acs.joc.0c01939

  日期：2020.12.18

  report on the chemical synthesis of residue-selectively 13C- and 2H-labeled oligosaccharides and their use in conformational analysis. 1H NMR measurements of such double isotope-labeled compounds can provide a great deal of information on the dihedral angles across glycosidic linkages. We demonstrated this method in the conformational analyses of some linear and branched β(1,3)-glucan oligosaccharides

  寡糖的构象分析是糖生物学中的一个基本问题。原子选择性13 C标记的寡糖的NMR测量提供了有关其构象的有价值的信息，使用未标记的寡糖是不可能的。然而，来自原子选择性标记的分子的可访问信息的数量是有限的。在这项工作中，我们报告了选择性残基13 C和2 H标记的寡糖的化学合成及其在构象分析中的用途。1个这种双同位素标记的化合物的1 H NMR测量可提供有关糖苷键跨二面角的大量信息。我们在一些线性和分支的β（1,3）-葡聚糖寡糖的构象分析中证明了该方法。
• Synthesis of β(1,3) oligoglucans exhibiting a Dectin-1 binding affinity and their biological evaluation
  作者：Hiroshi Tanaka、Tetsuya Kawai、Yoshiyuki Adachi、Shinya Hanashima、Yoshiki Yamaguchi、Naohito Ohno、Takashi Takahashi

  DOI：10.1016/j.bmc.2012.04.017

  日期：2012.6

  In this report, we describe the synthesis and biological evaluation of beta(1,3) oligosaccharides that contain an aminoalkyl group and their biological evaluation. A 2,3 diol glycoside with a 4,6 benzylidene protecting group was used as an effective glycosyl acceptor for the synthesis of some beta(1,3) linked glycosides. The use of a combination of a linear tetrasaccharide and a branched pentasaccharide as glycosyl donors led to the preparation of beta(1,3) linear octa-to hexadecasaccharides and branched nona-to heptadecasaccharides in good total yields. Measurements of the competitive effects of the oligosaccharides on the binding of a soluble form of Dectin-1 to a solid-supported Schizophyllan (SPG) revealed that the branched heptadecasaccharide and the linear hexadecasaccharides also have binding activity for Dectin-1. In addition, the two oligosaccharides, both of which contain a beta(1,3) hexadecasaccharide backbone, exhibited agonist activity in a luciferase-assisted NF-kappa B assay. STD-NMR analyses of complexes of Dectin-1 and the linear hexadecasaccharides clearly indicate Dectin-1 specifically recognizes the sugar part of the oligosaccharides and not the aminoalkyl chain. (C) 2012 Published by Elsevier Ltd.