2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose | 138902-18-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose
• 英文别名: (2R,3R,4R,5S,6R)-3-azido-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol
• CAS: 138902-18-8
• 化学式: C₂₇H₂₉N₃O₅
• 分子量: 475.544
• InChiKey: HWPBAVIEENPTJY-RFNQJFSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose 在 盐酸 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 三氟甲磺酸酐 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 72.0h， 生成 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose 、 2-Azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucose
  参考文献：
  名称：

  A Synthetic Approach to Aromatic Aminoglycoside as a Neamine Mimic

  摘要：

  This paper describes the synthetic approach to an aromatic alpha-glycoside as a mimic of neamine, which is a common core structure of some aminoglycoside antibiotics. We achieved the synthesis of the protected precursor of the neamine mimic, 4-(2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyloxy)-1,3-phenylenediamine, from N-acetyl-D-glucosamine and 2,4-diaminophenol as the starting materials using a glycosylation technique.

  DOI：

  10.3987/com-11-s(p)69

文献信息

• Synthesis and biological activity of phosphoglycolipids from Thermus thermophilus
  作者：Yukari Fujimoto、Kunihiro Mitsunobe、Satoko Fujiwara、Motoko Mori、Masahiro Hashimoto、Yasuo Suda、Shoichi Kusumoto、Koichi Fukase

  DOI：10.1039/c3ob40899j

  日期：——

  opposite configuration at the diacyl glycerol moiety, were also synthesized. The biological activities of the synthesized compounds were elucidated with cytokine inductions (IL-6 and TNF-α). A synthetic phosphoglycolipid with a natural-type diacyl glycerol configuration showed apparent immunostimulatory activity, whereas its diastereomer did not. The present study revealed that the configuration at the

  极端嗜热菌Thermus thermophilus在细胞表面具有非常独特的糖脂。嗜热链球菌的酸性免疫刺激性磷酸糖脂首次使用新开发的糖基化方法，使用3-硝基吡啶基（3NPy）和4,6-二甲氧基-1,3,5-三嗪-2-基（DMT）糖苷作为糖基供体进行合成。还合成了磷酸糖脂的类似物，其包括在二酰基甘油部分具有相反构型的非对映异构体。通过细胞因子诱导（IL-6和TNF-α）阐明了合成化合物的生物学活性。具有天然型二酰基甘油构型的合成磷酸糖脂显示出明显的免疫刺激活性，而其非对映异构体则没有。本研究表明，磷酸糖脂的二酰基甘油部分的构型对于免疫刺激很重要，
• Borinic Acid Catalyzed Stereo- and Regioselective Couplings of Glycosyl Methanesulfonates
  作者：Kyan A. D’Angelo、Mark S. Taylor

  DOI：10.1021/jacs.6b06943

  日期：2016.8.31

  catalyst, room temperature). The borinic acid catalyst not only influences site-selectivity via activation of 1,2- or 1,3-diol motifs, but also has a pronounced effect on the stereochemical outcome: 1,2-trans-linked disaccharides are obtained selectively in the absence of neighboring group participation. Reaction progress kinetic analysis was used to obtain insight into the mechanism of glycosylation, both

  在二芳基硼酸催化剂存在下，糖基甲磺酸盐与部分保护的吡喃糖苷和呋喃糖苷受体进行区域和立体选择性偶联。甲磺酸酯供体由糖基半缩醛原位制备，并在温和、操作简单的条件下（胺碱、有机硼催化剂、室温）偶联。硼酸催化剂不仅通过 1,2- 或 1,3- 二醇基序的活化影响位点选择性，而且对立体化学结果有显着影响：在不存在的情况下选择性地获得 1,2-反式连接的二糖邻组参与。反应进程动力学分析用于深入了解糖基化机制，在催化剂存在和不存在的情况下，而甲磺酸酯异头物的相互转化率则由核磁共振交换光谱法 (EXSY) 确定。总之，结果表明，尽管未催化和催化反应产生相反的立体化学结果，但两者都通过缔合机制进行。
• One-Step TEMPO-Catalyzed and Water-Mediated Stereoselective Conversion of Glycals into 2-Azido-2-deoxysugars with a PIFA–Trimethylsilyl Azide Reagent System
  作者：Ande Chennaiah、Yashwant D. Vankar

  DOI：10.1021/acs.orglett.8b00814

  日期：2018.5.4

  An unprecedented water-mediated and TEMPO-catalyzed, one-step, highly regiospecific and stereoselective functionalization of glycals to 2-azido-2-deoxysugars has been developed using a PIFA-Me3SiN3 reagent system in the presence of Bu4NHSO4 as a phase-transfer catalyst. The method is metal-free, proceeds under mild reaction conditions, and tolerates a variety of protecting groups. Using this method, the synthesis of an important trisaccharide unit bound by the monoclonal anti-I Ma antibody has also been demonstrated.
• A Synthetic Approach to Aromatic Aminoglycoside as a Neamine Mimic
  作者：Takashi Yamanoi、Ryo Inoue、Sho Matsuda、Yoshiki Oda、Hirofumi Ooyama、Akihiro Yoshida、Keita Hamasaki

  DOI：10.3987/com-11-s(p)69

  日期：——

  This paper describes the synthetic approach to an aromatic alpha-glycoside as a mimic of neamine, which is a common core structure of some aminoglycoside antibiotics. We achieved the synthesis of the protected precursor of the neamine mimic, 4-(2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyloxy)-1,3-phenylenediamine, from N-acetyl-D-glucosamine and 2,4-diaminophenol as the starting materials using a glycosylation technique.