4-azido-4,6-dideoxy-1,2,3-tri-O-acetyl-α-D-mannopyranose | 121803-81-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-azido-4,6-dideoxy-1,2,3-tri-O-acetyl-α-D-mannopyranose
• 英文别名: 1,2,3-tri-O-acetyl-4-azido-4,6-dideoxy-α-D-mannopyranoside；[(2R,3S,4S,5R,6R)-2,3-diacetyloxy-5-azido-6-methyloxan-4-yl] acetate
• CAS: 121803-81-4
• 化学式: C₁₂H₁₇N₃O₇
• 分子量: 315.283
• InChiKey: SLKKGXNJIFKYBE-FSVXGXJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-azido-4,6-dideoxy-1,2,3-tri-O-acetyl-α-D-mannopyranose 在 palladium on activated charcoal 4 A molecular sieve 、 三氟化硼乙醚 、 硫化氢 、 氢气 、 sodium methylate 、 对甲苯磺酸 、 三氟甲烷磺酸甲酯 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 20.0~50.0 ℃ 、5.0 kPa 条件下， 反应 130.0h， 生成 methyl O-(4,6-dideoxy-4-formamido-α-D-mannopyranosyl)-(1->3)-O-(4,6-dideoxy-4-formamido-α-D-mannopyranosyl)-(1->2)-O-(4,6-dideoxy-4-formamido-α-D-mannopyranosyl)-(1->2)-O-(4,6-dideoxy-4-formamido-α-D-mannopyranosyl)-(1->2)-4,6-dideoxy-4-formamido...
  参考文献：
  名称：

  Peters, Thomas; Bundle, David R., Canadian Journal of Chemistry, 1989, vol. 67, p. 497 - 502

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基 4-叠氮基-4,6-二脱氧吡喃甘露糖苷 在 硫酸 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 4-azido-4,6-dideoxy-1,2,3-tri-O-acetyl-α-D-mannopyranose
  参考文献：
  名称：

  Peters, Thomas; Bundle, David R., Canadian Journal of Chemistry, 1989, vol. 67, p. 497 - 502

  摘要：

  DOI：

文献信息

• Design and Synthesis of a Universal Antigen to Detect Brucellosis
  作者：Julie Guiard、Eugenia Paszkiewicz、Joanna Sadowska、David R. Bundle

  DOI：10.1002/anie.201302303

  日期：2013.7.8

  Upgrading diagnostics: A universal antigen has been prepared for the detection of brucellosis caused by any Brucella species that express a smooth lipopolysaccharide. This nonasaccharide, which encompasses Brucella A‐ and M‐antigenic determinants, is uniquely available only by chemical synthesis.

  诊断升级：已准备了一种通用抗原，用于检测由表达光滑脂多糖的任何布鲁氏菌属引起的布鲁氏菌病。这种包含布鲁氏菌A和M抗原决定簇的九糖，只有通过化学合成才能唯一获得。
• OLIGOSACCHARIDE CONJUGATES AND METHODS OF USE
  申请人：THE SECRETARY OF STATE FOR ENVIRNMENT, FOOD AND RURAL AFFAIRS

  公开号：US20160067345A1

  公开（公告）日：2016-03-10

  There is provided a method of detecting in a sample the presence of an anti-M and/or anti-A and/or anti-C/Y anti-body, the method comprising contacting the sample with a diagnostic conjugate provided according to the invention, comprising an oligosaccharide which comprises at least two units of 4,6-dideoxy-4-acylamido-α-pyranose and comprising at least one -(1-3)-link between adjacent 4,6-dideoxy-4-acylamido-α-pyranose units, in which the carbon at position 5 in the pyranose is linked to an R group, where R is independently selected from —CH 2 OH, —H or an alkyl group having at least one C atom, the oligosaccharide being covalently linked to a non-saccharide molecule or to a surface.

  本发明提供了一种检测样品中抗-M和/或抗-A和/或抗C/Y抗体存在的方法，该方法包括将样品与根据本发明提供的诊断共轭物接触，所述诊断共轭物包括寡糖，其包含至少两个4,6-二脱氧-4-酰胺基-α-吡喃糖单元，并且包含至少一个相邻的4,6-二脱氧-4-酰胺基-α-吡喃糖单元之间的-(1-3)-键，其中在吡喃糖的5号碳与R基连接，其中R独立选择自-CH2OH，-H或至少具有一个C原子的烷基基团，所述寡糖与非糖分子或表面共价连接。
• Oligosaccharide conjugates and methods of use
  申请人：THE SECRETARY OF STATE FOR ENVIRONMENT, FOOD AND RURAL AFFAIRS

  公开号：US10207006B2

  公开（公告）日：2019-02-19

  There is provided a method of detecting in a sample the presence of an anti-M and/or anti-A and/or anti-C/Y antibody, the method comprising contacting the sample with a diagnostic conjugate provided according to the invention, comprising an oligosaccharide which comprises at least two units of 4,6-dideoxy-4-acylamido-α-pyranose and comprising at least one -(1-3)- link between adjacent 4,6-dideoxy-4-acylamido-α-pyranose units, in which the carbon at position 5 in the pyranose is linked to an R group, where R is independently selected from —CH2OH, —H or an alkyl group having at least one C atom, the oligosaccharide being covalently linked to a non-saccharide molecule or to a surface.

  本发明提供了一种检测样品中是否存在抗-M 和/或抗-A 和/或抗-C/Y 抗体的方法，该方法包括将样品与根据本发明提供的诊断共轭物接触，该诊断共轭物由寡糖组成，寡糖包括至少两个 4,6-二脱氧-4-酰氨基-α-吡喃糖单元，相邻的 4、6-二脱氧-4-酰氨基-α-吡喃糖单元之间至少有一个-(1-3)-连接，其中吡喃糖第 5 位的碳与一个 R 基相连，其中 R 独立地选自-CH2OH、-H 或至少有一个 C 原子的烷基，寡糖与非糖分子或表面共价连接。
• PETERS, THOMAS;BUNDLE, DAVID R., CAN. J. CHEM., 67,(1989) N, C. 497-502
  作者：PETERS, THOMAS、BUNDLE, DAVID R.

  DOI：——

  日期：——
• Synthesis of a spacer-armed disaccharide structurally related to the M antigenic fragment of Brucella O-polysaccharides
  作者：Yu. E. Tsvetkov、N. E. Nifantiev

  DOI：10.1007/s11172-023-4079-4

  日期：2023.11