4-methylphenyl 2-azido-2-deoxy-1-thio-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylphenyl 2-azido-2-deoxy-1-thio-D-glucopyranoside
• 英文别名: (2R,3S,4R,5R,6R)-5-azido-2-(hydroxymethyl)-6-(4-methylphenyl)sulfanyloxane-3,4-diol
• 化学式: C₁₃H₁₇N₃O₄S
• 分子量: 311.362
• InChiKey: LGUQMWRHZKDLEU-SYLRKERUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-methylphenyl 2-azido-2-deoxy-1-thio-D-glucopyranoside 在 吡啶 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 p-tolyl 2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  d-氨基葡萄糖的α-选择性糖基化的有效策略及其在包含多个α-连接的GlcNAc残基的细菌荚膜多糖重复单元的合成中的应用。

  摘要：

  基于TolSCl / AgOTf促进系统和相应叠氮基供体6-O上的官能团的协同α导向作用，开发了一种高效的α-选择性糖基化方法，用于合成2-脱氧-2-氨基-d-糖苷。 -位发挥空间β-屏蔽作用或远程参与糖基化反应。它的实用性已通过广泛的单糖糖基受体和鲍曼不动杆菌K47荚膜多糖挑战性五糖重复单元的第一个反应罐合成进行了验证。

  DOI：

  10.1021/acs.orglett.0c00101
• 作为产物：
  描述：

  2-叠氮基-2-脱氧-D-吡喃葡萄糖1,3,4,6-四乙酸酯 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 4-methylphenyl 2-azido-2-deoxy-1-thio-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and High-Throughput Screening of N-Acetyl-β-hexosaminidase Inhibitor Libraries Targeting Osteoarthritis

  摘要：

  C1 Nitrogen iminocyclitols are potent inhibitors of N-acetyl-beta-hexosaminidases. Given hexosaminidases' important roles in osteoarthritis, we developed two straightforward and efficient syntheses of C1 nitrogen iminocyclitols from two readily available starting materials, D-mannosamine hydrochloride and the microbial oxidation product of fructose. A diversity-oriented synthetic strategy was then performed by coupling these core structures with various aldehydes, carboxylic acids, and alkynes to generate three separate libraries. High-throughput screening of the generated libraries with human N-acetyl-beta-hexosaminidases produced only moderate inhibitory activities. However, the synthetic approach and screening strategy for these compounds will be applied to develop new potent inhibitors of human N-acetyl-beta-hexosaminidases, particularly when combined with the structural information of these enzymes.

  DOI：

  10.1021/jo049355h

文献信息

• Synthesis of the Heparin-Based Anticoagulant Drug Fondaparinux
  作者：Cheng-Hsiu Chang、Larry S. Lico、Teng-Yi Huang、Shu-Yi Lin、Chi-Liang Chang、Susan D. Arco、Shang-Cheng Hung

  DOI：10.1002/anie.201404154

  日期：2014.9.8

  Fondaparinux, a synthetic pentasaccharide based on the heparin antithrombin‐binding domain, is an approved clinical anticoagulant. Although it is a better and safer alternative to pharmaceutical heparins in many cases, its high cost, which results from the difficult and tedious synthesis, is a deterrent for its widespread use. The chemical synthesis of fondaparinux was achieved in an efficient and

  Fondaparinux是一种基于肝素抗凝血酶结合结构域的合成五糖，是公认的临床抗凝剂。尽管在许多情况下它是替代药物肝素的更好，更安全的替代方法，但由于合成困难而乏味，其高昂的成本阻碍了其广泛使用。磺达肝素的化学合成以有效和简洁的方式从可商购获得d -葡糖胺，二丙酮α- d葡萄糖和五-O-乙酰基d -葡萄糖。该方法涉及适当功能化的构建基块，这些构建基块易于使用，并使用共享的中间体和一系列单反应，从而显着减少了合成工作量并提高了收率。
• A green and regioselective acetylation of thioglycoside with ethyl acetate
  作者：Pi-Hui Liang、Yin-Jen Lu、Ting-Hsuan Tang

  DOI：10.1016/j.tetlet.2010.10.135

  日期：2010.12

  Treatment of saccharidic polyols in ethyl acetate with catalytic sulfuric acid leads to the corresponding primary monoacetate derivatives in good yields. The transesterification was realized by simple stirring without rigorous exclusion of moisture or oxygen. Our protocol is applicable to the regioselective mono-acetylation of amino sugars having different substituents at the 2-positions. (C) 2010 Elsevier Ltd. All rights reserved.
• OLIGOSACCHARIDE LINKER, LINKER-PAYLOAD COMPRISING THE SAME AND GLYCAN CHAIN-REMODELED ANTIBODY-DRUG CONJUGATE, PREPARATION METHODS AND USES THEREOF
  申请人：GENEQUANTUM HEALTHCARE CO., LTD.

  公开号：US20240082419A1

  公开（公告）日：2024-03-14

  The present disclosure further relates to a linker-payload compound including an oligosaccharide group, especially a disaccharide group, where the oligosaccharide group is linked to the remainder of the compound by an amide bond. The present disclosure further relates to an antibody-drug conjugate (ADC) containing the linker-payload compound, where the glycan chain in an antibody is remodeled with the oligosaccharide moiety in the linker-payload compound. The present disclosure further relates to preparation methods and use of the above-mentioned substances.
• Synthesis and High-Throughput Screening of <i>N</i>-Acetyl-β-hexosaminidase Inhibitor Libraries Targeting Osteoarthritis
  作者：Junjie Liu、Mehdi M. D. Numa、Haitian Liu、Shi-Jung Huang、Pamela Sears、Alexander R. Shikhman、Chi-Huey Wong

  DOI：10.1021/jo049355h

  日期：2004.9.1

  C1 Nitrogen iminocyclitols are potent inhibitors of N-acetyl-beta-hexosaminidases. Given hexosaminidases' important roles in osteoarthritis, we developed two straightforward and efficient syntheses of C1 nitrogen iminocyclitols from two readily available starting materials, D-mannosamine hydrochloride and the microbial oxidation product of fructose. A diversity-oriented synthetic strategy was then performed by coupling these core structures with various aldehydes, carboxylic acids, and alkynes to generate three separate libraries. High-throughput screening of the generated libraries with human N-acetyl-beta-hexosaminidases produced only moderate inhibitory activities. However, the synthetic approach and screening strategy for these compounds will be applied to develop new potent inhibitors of human N-acetyl-beta-hexosaminidases, particularly when combined with the structural information of these enzymes.
• Efficient Strategy for α-Selective Glycosidation of <scp>d</scp>-Glucosamine and Its Application to the Synthesis of a Bacterial Capsular Polysaccharide Repeating Unit Containing Multiple α-Linked GlcNAc Residues
  作者：Yanxin Zhang、Han Zhang、Ying Zhao、Zhongwu Guo、Jian Gao

  DOI：10.1021/acs.orglett.0c00101

  日期：2020.2.21

  An efficient α-selective glycosylation method was developed for the synthesis of 2-deoxy-2-amino-d-glucosides based on synergetic α-directing effects of the TolSCl/AgOTf promotion system and the functional groups at the corresponding azido donor 6-O-position to exert steric β-shielding effect or remote participation in the glycosylation reaction. Its practicability was verified with a wide range of

  基于TolSCl / AgOTf促进系统和相应叠氮基供体6-O上的官能团的协同α导向作用，开发了一种高效的α-选择性糖基化方法，用于合成2-脱氧-2-氨基-d-糖苷。 -位发挥空间β-屏蔽作用或远程参与糖基化反应。它的实用性已通过广泛的单糖糖基受体和鲍曼不动杆菌K47荚膜多糖挑战性五糖重复单元的第一个反应罐合成进行了验证。