ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside | 848828-33-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside
• 英文别名: ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl (1→2) 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside
• CAS: 848828-33-1
• 化学式: C₂₈H₃₆N₆O₆S
• 分子量: 584.696
• InChiKey: KWQAXNCCZDWRID-WIEAFOMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  163.9
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside 在 氢氧化钾 、 硫化氢 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 吡啶 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 ethyl 3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-methyl-α-D-mannopyranosyl-(1->2)-3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  热力学控制下的糖基化：从全功能化构建块合成霍乱弧菌 O:1 血清型小川的 O-SP 的二糖和六糖片段

  摘要：

  霍乱弧菌 O:1、血清型 Ogawa 31 的 O-SP 六糖的已知 5-(甲氧基羰基)戊基 α-糖苷是从配备侧链的二糖结构单元中新制备的。中间体四糖 25 由二糖糖基受体 11 和 (12) 连接的二糖硫糖苷糖基供体 8 制备，在下游末端的 C-2 处具有（非参与）糖部分。当以常规方式进行时（在室温或低于 0 °C 的温度下），在没有嵌合辅助的情况下进行的 11 糖基化显示出较差的立体选择性，但通过热力学控制可以显着改善 1,2-反式糖苷键的形成。这种针对 31 的综合策略比逐步方法更有效，后者基于

  DOI：

  10.1002/ejoc.200600851
• 作为产物：
  描述：

  ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)(4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以81%的产率得到ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  检测布鲁氏菌病通用抗原的设计与合成

  摘要：

  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。

  DOI：

  10.1002/anie.201302303

文献信息

• Immunogens from a synthetic hexasaccharide fragment of the O-SP of Vibrio cholerae O:1, serotype Ogawa
  作者：Rina Saksena、Jian Zhang、Pavol Kováč

  DOI：10.1016/j.tetasy.2004.11.021

  日期：2005.1

  The known 5-(methoxycarbonyl)pentyl alpha-glycoside of the hexasaccharide of Vibrio cholerae O:1, serotype Ogawa 24 was newly prepared. The efficiency of construction of the hexasaccharide from the disaccharide glycosyl acceptor 6 and each of the two tetrasaccharide glycosyl donors 16, and 18, as an alternative to the iterative coupling of the disaccharide glycosyl donor 7 with 6, was evaluated. Compound 24 was treated with each of hydrazine hydrate, ethylenediamine. and hexamethylenediamine to give ligands 25, 27, and 29, respectively, equipped with different linkers. Reaction of the foregoing compounds with squaric acid diethyl ester. and the reactions of the thus formed monoesters 26, 28, and 30 with BSA were evaluated. The rate of formation of the corresponding monoester was higher with hydrazide 25 than with amines 27 and 29. whose reaction rates were virtually the same. Reactions of squaric acid derivatives 26, 28, and 30 with BSA were conducted under the same conditions (reaction temperature, ligand-BSA ratio, and concentration with respect to the hapten) and targeted for neoglycoconjugates with 24-BSA ratio of similar to5. Monitoring the conversions by SELDI-TOF mass spectrometry in conjunction with the ProteinChip(R) system made it possible to conduct the conjugations in controlled fashion, and to terminate the reactions when the desired carbohydrate-protein ratios were reached. Products from 26, 28, and 30, neoglycoconjugates 31-33, containing 4.9, 5.0, and 5.1 moles of 24/BSA, respectively, were obtained in 87-93% yields. When the conjugation started with the initial molar carbohydrate-protein ratio of 15:1, the final molar carbohydrate-BSA ratio reached after 14 days with ligands 26, 28, and 30 was 9.0, 11.0, and 9.1, respectively. (C) 2004 Elsevier Ltd. All rights reserved.