1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-methyl-β-D-glucopyranose | 174911-12-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-methyl-β-D-glucopyranose
• 英文别名: (1R,2S,3R,4R,5R)-4-azido-2-methoxy-3-phenylmethoxy-6,8-dioxabicyclo[3.2.1]octane
• CAS: 174911-12-7
• 化学式: C₁₄H₁₇N₃O₄
• 分子量: 291.307
• InChiKey: YYYBNJSUBXYZKH-DHGKCCLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-methyl-β-D-glucopyranose 在 二甲胺 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 生成 Acetic acid (2R,3S,4R,5R)-5-azido-4-benzyloxy-6-fluoro-3-methoxy-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Analogues of d -glucosaminylphosphatidylinositol: synthesis of the glycosyl donors

  摘要：

  Appropriately protected deoxy and other analogues of 2-azido-2-deoxy-D-glucopyranosyl fluoride have been synthesised preparatory to inclusion into analogues of the D-glucosaminylphosphatidylinositol 1. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01900-6
• 作为产物：
  描述：

  1,6-anhydro-4-O-methyl-2-O-p-toluenesulphonyl-β-D-glucopyranose 在 叠氮化锂 、 sodium methylate 、 sodium hydride 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-methyl-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis and biological activity of oligomer-model compounds containing units of a key platelet-binding disaccharide of heparin

  摘要：

  A key disaccharide unit in heparin, O-(2-deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1-->4)-2-O-sulfo-alpha-L-idopyranosyluronic acid, was previously found to be responsible for the binding interaction of heparin to platelets. A clustering effect to enhance the binding was found to be dependent on the number and frequency of the disaccharide units in a heparin molecule. To systematically examine the clustering effect, three oligomer-model compounds containing two or three units of the disaccharide were synthesized. These compounds inhibited (3)H-Iabelled heparin binding to human platelets more strongly than a compound containing only one unit of the disaccharide, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01084-9

文献信息

• Synthesis and biological activity of a model disaccharide containing a key unit in heparin for binding to platelets
  作者：Yasuo Suda、Karyn Bird、Takaaki Shiyama、Shuhei Koshida、Dalila Marques、Koichi Fukase、Michael Sobel、Shoichi Kusumoto

  DOI：10.1016/0040-4039(95)02346-1

  日期：1996.2

  specific site(s) in heparin necessary for binding to platelets, synthesis of a model compound containing the disaccharide sequence, O-(2-deoxy-2-sulfamido-6-O-sulfo-α-D-glucopyranosyl)-(1→4)-2-O-sulfo-α-L-idopyranuronic acid, found in heparin was performed by α-selective glycosidation using a phenyl thioglycoside as a donor. The compound inhibited 125I-labelled heparin binding to human platelets to

  为了确定肝素中与血小板结合所必需的特定位点，合成包含二糖序列O-（2-脱氧-2-磺酰胺基-6-O-磺基-α-D-吡喃葡萄糖基）-的模型化合物肝素中发现的（1→4）-2-O-磺基-α-L-异吡喃葡萄糖醛酸是通过使用苯基硫代糖苷作为供体的α-选择性糖苷化而进行的。与通过肝素酶I消化获得的肝素衍生的二糖相比，该化合物抑制125 I标记的肝素与人血小板的结合程度更大，但每个分子中包含相同数量的硫酸根。
• Investigating Glycol-Split-Heparin-Derived Inhibitors of Heparanase: A Study of Synthetic Trisaccharides
  作者：Minghong Ni、Stefano Elli、Annamaria Naggi、Marco Guerrini、Giangiacomo Torri、Maurice Petitou

  DOI：10.3390/molecules21111602

  日期：——

  structure glycol-split uronic acid moieties probably responsible for their strong inhibitory activity. We describe here the total chemical synthesis of the trisaccharide GlcNS6S-GlcA-1,6anGlcNS (1) and its glycol-split (gs) counterpart GlcNS6S-gsGlcA-1,6anGlcNS (2) from glucose. As expected, in a heparanase inhibition assay, compound 2 is one order of magnitude more potent than 1. Using molecular modeling

  乙酰肝素酶是唯一已知的能够裂解硫酸乙酰肝素的内切糖苷酶。Roneparstat和necuparanib是从肝素中获得的乙酰肝素酶抑制剂，目前正在人类中作为潜在的抗癌药物进行测试，其结构中含有乙二醇分裂的糖醛酸部分，可能是其强大的抑制活性。我们在这里描述了三糖GlcNS6S-GlcA-1,6anGlcNS（1）及其乙二醇拆分（gs）对应物GlcNS6S-gsGlcA-1,6anGlcNS（2）的总化学合成。不出所料，在乙酰肝素酶抑制试验中，化合物2的效力比1高一个数量级。使用分子建模技术，我们创建了1和2的3D模型，并已通过NOESY NMR实验验证。纯合成寡糖已使乙二醇拆分的葡萄糖醛酸的构象得以首次深入研究。以1的结构引入乙二醇拆分单元可增加构象柔韧性，并缩短两种氨基葡萄糖动机之间的距离，从而促进与乙酰肝素酶的相互作用。然而，通过比较2和ronparstat的相对活性，我们可以得出结论，乙