1,3,4,6-tetra-O-acetyl-2-benzamido-2-deoxy-β-D-glucopyranose | 10385-49-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-benzamido-2-deoxy-β-D-glucopyranose
• 英文别名: [(2R,3S,4R,5R,6S)-3,4,6-triacetyloxy-5-benzamidooxan-2-yl]methyl acetate
• CAS: 10385-49-6
• 化学式: C₂₁H₂₅NO₁₀
• 分子量: 451.43
• InChiKey: YCDLVTWRPTYDJW-DRJBRKBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-benzamido-2-deoxy-β-D-glucopyranose 在 calcium sulfate 、 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 生成 2-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)<2,1-d>-2-oxazoline
  参考文献：
  名称：

  氯化铁催化偶合保护2-氨基-2-脱氧-d-吡喃葡萄糖的糖苷和二糖

  摘要：

  描述了受保护的2-酰基氨基-2-脱氧-β-D-吡喃葡萄糖1-乙酸盐的氯化铁催化的羟基化合物的糖基化。除了醇与2-乙酰氨基-1,3,4,6-四-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖（3），烯丙基（和其他烷基）β-糖苷是从3的N-苯甲酰基，N-苯氧基乙酰基，N-甲氧基乙酰基，N-氯乙酰基和N-邻苯二甲酰基同系物获得的。除了N-邻苯二甲酰基衍生物以外，后一种化合物在不存在醇类反应物的情况下生成恶唑啉。化合物3和相关的N-苯甲酰基，N-氯乙酰基，N-乙酰基-3,4,6-三-O-苄基和N-乙酰基-4-O-乙酰基-3,6-二-O-苄基衍生物将其与一种或多种受保护的糖偶联以形成受保护的，β-连接的二糖。受体6位的偶联反应顺利进行，收率为67-80％。为了在位置3和4上成功偶联，需要较长的反应时间和多次添加糖基供体，收率范围从60％到低至30％。1,3,4,6-四-O-乙酰基-2-（氯乙酰胺基）-2-

  DOI：

  10.1016/0008-6215(85)85205-8
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-(4-methoxybenzylidene)amino-β-D-glucopyranose 在 吡啶 、 盐酸 、 苯甲酰氯 、 丙酮 作用下， 生成 1,3,4,6-tetra-O-acetyl-2-benzamido-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Bergmann; Zervas, Chemische Berichte, 1931, vol. 64, p. 975,978

  摘要：

  DOI：

文献信息

• 一种葡萄糖酰胺类化合物及其制备与应用
  申请人：浙江工业大学

  公开号：CN106565797B

  公开（公告）日：2019-06-14

  本发明涉及一种含葡萄糖酰胺类化合物及其制备方法，所述的葡萄糖酰胺类化合物，其结构如式(I)所示：式(I)中，R为甲氧基、硝基、氨基、羟基、C1～4的烷基或卤素,n为取代基个数，n为1或2。本发明所述的葡萄糖酰胺类化合物制备简单，具有优异的植物诱抗活性，可用作防治黄瓜细菌性角斑病、黄瓜褐斑病、番茄晚疫病植物诱抗剂中的应用，本发明还涉及含有该类化合物的植物诱抗剂。
• SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF
  申请人：Vocadlo David

  公开号：US20100016386A1

  公开（公告）日：2010-01-21

  The invention provides compounds of formula (I) for selectively inhibiting glycosidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds The invention also provides methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, accumulation or deficiency of O-GlcNAc

  该发明提供了式(I)的化合物，用于选择性抑制酶，该化合物的前药以及包括化合物或化合物前药的药物组合物。该发明还提供了治疗与O-GlcNAcase缺乏或过度表达，O-GlcNAc积累或缺乏相关的疾病和障碍的方法。
• WO2008/25170
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and evaluation of anti-tubercular activity of new dithiocarbamate sugar derivatives
  作者：Yasuhiro Horita、Takemasa Takii、Ryuji Kuroishi、Taku Chiba、Kenji Ogawa、Laurent Kremer、Yasuo Sato、YooSa Lee、Tomohiro Hasegawa、Kikuo Onozaki

  DOI：10.1016/j.bmcl.2010.12.084

  日期：2011.2

  The present study was undertaken to optimize the anti-tubercular activity of 2-acetamido-2-deoxy-beta-D-glucopyranosyl N,N-dimethyldithiocarbamate (OCT313, Glc-NAc-DMDC), a lead compound previously reported by us. Structural modifications of OCT313 included the replacements of the DMDC group at C-1 by pyrrolidine dithiocarbamate (PDTC) and the acetyl group at C-2 by either propyl, butyl, benzyl or oleic acid groups. The antimycobacterial activities of these derivatives were evaluated against Mycobacterium tuberculosis (MTB). Glc-NAc-pyrrolidine dithiocarbamate (OCT313HK, Glc-NAc-PDTC) exhibited the most potent anti-tubercular activity with the minimal inhibitory concentration (MIC) of 6.25-12.5 mu g/ml. The antibacterial activity of OCT313HK was highly specific to MTB and Mycobacterium bovis BCG, but not against Mycobacterium avium, Mycobacterium smegmatis, Staphylococcus aureus or Escherichia coli. Importantly, OCT313HK was also effective against MTB clinical isolates, including multidrug-resistant (MDR) and extensively drug-resistant (XDR) strains. Interestingly, OCT313HK was exerted the primary bactericidal activity, and it was also exhibited the bacteriolytic activity at high concentrations. We next investigated whether the mycobacterial monooxygenase EthA, a common activator of thiocarbamide-containing antitubercular drugs, also activated OCT313HK. Contrary to our expectations, the anti-tubercular activity of dithiocarbamate sugar derivatives and dithiocarbamates were not dependent on ethA expression, in contrast to thiocarbamide-containing drugs. Overall, this study presents OCT313HK as a novel and potent compound against MTB, particularly promising to overcome drug resistance. (C) 2010 Elsevier Ltd. All rights reserved.
• 12. The action of periodic acid on glucosamine derivatives
  作者：Albert Neuberger

  DOI：10.1039/jr9410000047

  日期：——