1,2,3,6-tetra-O-acetyl-4-azido-4-deoxy-α-D-glucopyranose | 4098-00-4

• 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: 1,2,3,6-tetra-O-acetyl-4-azido-4-deoxy-α-D-glucopyranose
• 英文别名: [(2S,3R,4S,5R,6R)-4,5,6-triacetyloxy-3-azidooxan-2-yl]methyl acetate
• CAS: 4098-00-4
• 化学式: C₁₄H₁₉N₃O₉
• 分子量: 373.32
• InChiKey: BEUUZSCKQDTNMV-RGDJUOJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,2,3,6-tetra-O-acetyl-4-azido-4-deoxy-α-D-glucopyranose 在 4 A molecular sieve 、 乙酸肼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5-O-(4"-azido-2",3",6"-tri-O-acetyl-4"-deoxy-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine
  参考文献：
  名称：

  Pyranmycins, a Novel Class of Aminoglycosides with Improved Acid Stability:  The SAR of d-Pyranoses on Ring III of Pyranmycin

  摘要：

  The synthesis of a novel class of aminoglycosides, pyranmycins, is reported along with the structure activity relationship (SAR) of their antibacterial activity against Escherichia coli. Two pyranmycins show prominent activity (9 muM). Pyranmycins also manifest superior stability in acidic media. The SAR information will lead to the future designs of pyranmycin against drug resistant bacteria.

  DOI：

  10.1021/ol0269042
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 草酰氯 、 三氟甲磺酸酐 、 硫酸 、 4-甲基苯磺酸吡啶 、 四丁基碘化铵 、 sodium hydride 、 sodium cyanoborohydride 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 1,2,3,6-tetra-O-acetyl-4-azido-4-deoxy-α-D-glucopyranose
  参考文献：
  名称：

  Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin

  摘要：

  A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.

  DOI：

  10.1021/jo035290r

文献信息

• Efficient synthesis of a galectin inhibitor clinical candidate (TD139) using a Payne rearrangement/azidation reaction cascade
  作者：Jacob St-Gelais、Vincent Denavit、Denis Giguère

  DOI：10.1039/d0ob00910e

  日期：——

  Selective galectin inhibitors are valuable research tools and could also be used as drug candidates. In that context, TD139, a thiodigalactoside galectin-3 inhibitor, is currently being evaluated clinically for the treatment of idiopathic pulmonary fibrosis. Herein, we describe a new strategy for the preparation of TD139. Starting from inexpensive levoglucosan, we used a rarely employed reaction cascade:

  选择性半乳凝素抑制剂是有价值的研究工具，也可用作候选药物。在这种情况下，目前正在临床上评估TD139，一种硫代二糖半乳糖苷半乳糖凝集素3抑制剂，用于治疗特发性肺纤维化。在此，我们描述了TD139制备的新策略。从廉价的左旋葡聚糖开始，我们使用了很少使用的反应级联：Payne重排/叠氮化过程导致3-叠氮基-吡喃半乳糖。只需几个简单实用的步骤，即可将后者中间体有效转化为TD139。
• Total synthesis of sorbistin A1 and a positional isomer
  作者：Tomoya Ogawa、Kiyoaki Katano、Masanao Matsui

  DOI：10.1016/0040-4020(80)80148-7

  日期：1980.1

  Total synthesis of sorbistin A1 (1) and a positional isomer (7) is described for the first time in a regio- and stereo-controlled manner.

  首次以区域和立体控制的方式描述了山梨素A 1（1）和位置异构体（7）的全合成。
• <i>N</i>-Glycosylation with sulfoxide donors for the synthesis of peptidonucleosides
  作者：Margaux Beretta、Emilie Rouchaud、Lionel Nicolas、Jean-Pierre Vors、Thomas Dröge、Mazen Es-Sayed、Jean-Marie Beau、Stéphanie Norsikian

  DOI：10.1039/d1ob00493j

  日期：——

  The synthesis of glycopyranosyl nucleosides modified in the sugar moiety has been less frequently explored, notably because of the lack of a reliable method to glycosylate pyrimidine bases. Herein we report a solution in the context of the synthesis of peptidonucleosides. They were obtained after glycosylation of different pyrimidine nucleobases with glucopyranosyl donors carrying an azide group at

  糖部分修饰的吡喃葡萄糖核苷的合成较少被探索，特别是因为缺乏可靠的方法来糖基化嘧啶碱基。在此，我们报告了肽核苷合成背景下的解决方案。它们是通过在 C4 位上带有叠氮基团的吡喃葡萄糖基供体对不同的嘧啶核碱基进行糖基化后获得的。一项涉及不同异头离去基团（乙酸酯、苯亚砜和邻己炔基苯甲酸酯）的方法学研究表明，亚砜供体与作为促进剂的三甲基甲硅烷基三氟甲磺酸酯组合可产生最佳产率。
• Glycorandomization and production of novel vancomycin analogs
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20040259228A1

  公开（公告）日：2004-12-23

  The present invention provides combinatorial methods for rapidly generating a diverse library of glycorandomized structures, comprising incubating one or more aglycons and a pool of NDP-sugars in the presence of a glycosyltransferase. The glycosyltransferase may be one that is associated with or involved in production of natural secondary metabolites, or one which is putatively associated with or involved in production of natural secondary metabolites. The glycosyltransferase may show significant flexibility with respect to its NDP-sugar donors and/or its aglycons. NDP-sugar donors may be commercially available, or may be produced by utilizing mutant or wild type nucleotidyltransferases significant flexibility with respect to their substrates.

  本发明提供了快速生成多种糖随机化结构库的组合方法，包括在糖基转移酶存在下培养一种或多种琼脂糖和NDP-糖池。糖基转移酶可以是与天然次生代谢物的生产有关或参与生产的糖基转移酶，也可以是推测与天然次生代谢物的生产有关或参与生产的糖基转移酶。糖基转移酶在其 NDP-糖供体和/或其糖醛酸方面可以表现出很大的灵活性。NDP 糖供体可以从市场上买到，也可以通过利用突变型或野生型核苷酸转移酶对底物的极大灵活性来生产。
• Glucose Positions Affect the Phloem Mobility of Glucose–Fipronil Conjugates
  作者：Zhiwei Lei、Jie Wang、Genlin Mao、Yingjie Wen、Yuxin Tian、Huawei Wu、Yufeng Li、Hanhong Xu

  DOI：10.1021/jf5010429

  日期：2014.7.2

  In our previous work, a glucose-fipronil (GTF) conjugate at the C-1 position was synthesized via click chemistry and a glucose moiety converted a non-phloem-mobile insecticide fipronil into a moderately phloem-mobile insecticide. In the present paper, fipronil was introduced into the C-2, C-3, C-4, and C-6 positions of glucose via click chemistry to obtain four new conjugates and to evaluate the effects of the different glucose isomers on phloem mobility. The phloem mobility of the four new synthetic conjugates and GTF was tested using the Ricinus seedling system. The results confirmed that conjugation of glucose at different positions has a significant influence on the phloem mobility of GTF conjugates.