(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-formylphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-formylphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• 英文别名: (-)-4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)benzaldehyde；4-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside；(per-(O)-acetyl-β-D-galactopyranosyl)-4-oxybenzaldehyde；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(4-formylphenoxy)oxan-2-yl]methyl acetate
• 化学式: C₂₁H₂₄O₁₁
• 分子量: 452.415
• InChiKey: CDLMQSSFJCERSO-XDWAVFMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-formylphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 水 、 sodium methylate 、 2-巯基乙醇 、 magnesium chloride 、 β-galactosidase 作用下， 以 甲醇 、 苯 为溶剂， 反应 35.0h， 生成 对羟基苯甲醛
  参考文献：
  名称：

  A new class of bioactivable self-immolative N,O-ligands

  摘要：

  A hexadentate ligand built on an amine-bis(phenol) skeleton with an aminal, self-immolative moiety is presented. Synthesis of the ligand is convenient and relatively high yielded. Moreover, it enables synthesis of many derivatives, both in the amino-phenol and aminal fragment (various heterocycles). Once the final hexadentate ligand is synthesized via the Katritzky reaction, it becomes prone to hydrolysis. Bioactivation by beta-galactosidase cleaves the glycosylic bond and a spontaneous collapse of the aminal fragment occurs, thus leading to a pentadentate chelate. This bioactivation has been shown for pyrazole, 1,2,4-triazole and benzotriazole derivatives. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.017
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 氢溴酸 、 silver(l) oxide 作用下， 以 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 7.5h， 生成 (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-formylphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  新的半乳糖基化 N2O 供体三齿配体的合成和表征

  摘要：

  摘要 介绍了含有 4-[1-β-d-2,3,4,6-四-O-乙酰-半乳糖基)] 苯甲醛组的三种新型 N2O 供体配体的合成和表征。该组的插入旨在增加前药在肿瘤细胞中的吸收，并且是我们小组正在进行的三齿配体开发工作的一部分，以开发潜在的钴 (III) 前药。此处描述的合成路线允许分离纯配体，产率范围为 81-89%。最后，化合物通过 IR、NMR 和 HRMS (ESI+) 进行表征。图形概要

  DOI：

  10.1080/00397911.2019.1599953

文献信息

• Cyanuric Chloride Catalyzed Mild Protocol for Synthesis of Biologically Active Dihydro/Spiro Quinazolinones and Quinazolinone-glycoconjugates
  作者：Moni Sharma、Shashi Pandey、Kuldeep Chauhan、Deepty Sharma、Brijesh Kumar、Prem M. S. Chauhan

  DOI：10.1021/jo2020856

  日期：2012.1.20

  We have developed an efficient cyanuric chloride (2,4,6-trichloro-1,3,5-triazine, TCT) catalyzed approach for the synthesis of 2,3-dihydroquinazolin-4(1H)-one (3a–3x), 2-spiroquinazolinone (5, 7), and glycoconjugates of 2,3-dihydroquinazolin-4(1H)-one (10a, 10b) derivatives. The reaction allows rapid cyclization (8–20 min) with 10 mol % cyanuric chloride to give skeletal complexity in good to excellent

  我们已经开发了一种有效的氰尿酰氯（2,4,6-三氯-1,3,5-三嗪，TCT）催化方法，用于合成2,3-二氢喹唑啉-4（1 H）-一（3a – 3x） ，2- spiroquinazolinone（5，7），和2,3-二氢喹唑啉-4（1结合糖ħ） -酮（10A，10B）的衍生物。该反应允许使用10 mol％的氰尿酰氯快速环化（8–20分钟），从而以高至优异的产率获得复杂的骨架。我们相信，这种新颖的方法可能为容易产生新的生物活性喹唑啉酮打开大门。
• CASPASE-3-TRIGGERED MOLECULAR SELF-ASSEMBLING PET PROBES AND USES THEREOF
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US20200085980A1

  公开（公告）日：2020-03-19

  Embodiments of the synthesis, radiolabeling and biological applications of an activatable tracer that undergoes intramolecular cyclization and aggregation upon activation by cleavage of a blocking moiety are provided. The probes of the disclosure allow for target-controlled self-assembly of small molecules in living subjects for imaging and drug delivery. The aggregated nanoprobes of the disclosure may be detectable optically, by PET detection, magnetic resonance imaging, and the like depending on the detectable reporter attached to the nanoprobe.

  提供了一种可激活示踪剂的合成、放射标记和生物应用的实施例，该示踪剂在通过切除阻断基团激活时发生分子内环化和聚集。本公开的探针允许在活体中实现靶向控制的小分子自组装，用于成像和药物输送。根据附加到纳米探针上的可检测报告物，本公开的聚集纳米探针可以通过光学、PET检测、核磁共振成像等方式进行检测。
• Pd(II)‐Mediated C−H Activation for Cysteine Bioconjugation
  作者：James A. R. Tilden、Anneke T. Lubben、Shaun B. Reeksting、Gabriele Kociok‐Köhn、Christopher G. Frost

  DOI：10.1002/chem.202104385

  日期：2022.2.21

  Out of the box: A highly efficient bioconjugation strategy is reported utilising Pd(II) complexes prepared via C−H activation, which enable selective S-arylation of cysteine. These C−H activation complexes were prepared using common Pd(II) sources and without the need for a glovebox. A wide substrate scope is enabled by in situ generation of these complexes, which produce excellent conversions of a

  开箱即用：据报道，利用通过 C−H 激活制备的 Pd(II) 复合物，可以实现半胱氨酸的选择性S-芳基化，从而实现高效的生物共轭策略。这些 C−H 活化复合物是使用常见的 Pd(II) 源制备的，无需手套箱。这些复合物的原位生成可实现广泛的底物范围，从而产生模型三肽的出色转化，并能够芳基化完整蛋白质上的表面半胱氨酸。
• Contrast Agents for Magnetic Resonance Imaging
  申请人：Hasserodt Jens

  公开号：US20070218010A1

  公开（公告）日：2007-09-20

  The invention relates to contrast agents for magnetic resonance imaging comprising a chelating ligand and a transition metal ion, said ligand carrying a substituent capable of reacting chemically or biochemically with a target substance while bringing about a change in the spin state.

  这项发明涉及磁共振成像对比剂，包括螯合配体和过渡金属离子，所述配体携带能够在带来自旋态变化的同时与靶物质在化学或生物化学上发生反应的取代基。
• Probing Carbocatalytic Activity of Carbon Nanodots for the Synthesis of Biologically Active Dihydro/Spiro/Glyco Quinazolinones and Aza-Michael Adducts
  作者：Biju Majumdar、Sonam Mandani、Tamalika Bhattacharya、Daisy Sarma、Tridib K. Sarma

  DOI：10.1021/acs.joc.6b02914

  日期：2017.2.17

  the fluorescent carbon dots as an effective and recyclable carbocatalyst for the generation of carbon–heteroatom bond leading to quinazolinone derivatives and aza-Michael adducts under mild reaction conditions. The results establish this nanoscale form of carbon as an alternative carbocatalyst for important acid catalyzed organic transformations. The mild surface acidity of carbon dots imparted by

  本文中，我们报道了荧光碳点是有效且可回收的碳催化剂，可在温和的反应条件下生成碳-杂原子键，从而导致喹唑啉酮衍生物和氮杂-迈克尔加合物。结果确定了这种碳的纳米级形式，可作为重要的酸催化的有机转化的替代碳催化剂。在当前反应条件下，-COOH官能团赋予的碳点温和的表面酸性可以有效催化合成挑战性的螺/糖基喹唑啉酮的形成。