2-(4-methoxyphenoxy)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside | 1220097-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2-(4-methoxyphenoxy)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
• CAS: 1220097-91-5
• 化学式: C₂₂H₂₅N₃O₇
• 分子量: 443.456
• InChiKey: FRYWGTLMGCWCQL-YGBDOONVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  124.37
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenoxy)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 、 10% Pd(OH)2 on carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 2-(4-methoxyphenyl)-ethyl (2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Tri- and Disaccharide Fragments Related to the O-Antigen of Enteropathogenic Escherichia Coli O158

  摘要：

  Chemical synthesis of a tri- and a disaccharide related to the O-antigen of enteropathogenic E. coli O158 was achieved in high yield. In the disaccharide (2), one D-galactosamine unit is present in 1,2-cis-linked and the other is in the trans-orientation, and both of them were prepared from the same intermediate by tuning the reaction solvent. Yields were considerably high in all steps.

  DOI：

  10.1080/07328300903477804
• 作为产物：
  描述：

  2-(4-甲氧基苯氧基)-1-乙醇 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 16.0h， 生成 2-(4-methoxyphenoxy)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Tri- and Disaccharide Fragments Related to the O-Antigen of Enteropathogenic Escherichia Coli O158

  摘要：

  Chemical synthesis of a tri- and a disaccharide related to the O-antigen of enteropathogenic E. coli O158 was achieved in high yield. In the disaccharide (2), one D-galactosamine unit is present in 1,2-cis-linked and the other is in the trans-orientation, and both of them were prepared from the same intermediate by tuning the reaction solvent. Yields were considerably high in all steps.

  DOI：

  10.1080/07328300903477804

文献信息

• Synthesis of tri- and pentasaccharide fragments corresponding to the O-antigen of Shigella boydii type 6
  作者：Abhishek Santra、Anup Kumar Misra

  DOI：10.1016/j.tetasy.2010.10.032

  日期：2010.11

  A convenient synthetic strategy for the synthesis of the acidic pentasaccharide repeating unit and its trisaccharide fragment corresponding to the O-antigen of Shigella boydii type 6 has been successfully developed. A stereoselective sequential glycosylation method has been exploited to obtain the target tri- and pentasaccharide derivatives. Most of the synthetic intermediates were solid and prepared

  一种方便的合成策略，用于合成酸性五糖重复单元及其三糖片段（对应于波氏志贺氏菌的O-抗原）类型6已成功开发。已经开发了立体选择性顺序糖基化方法以获得目标三糖和五糖衍生物。大多数合成中间体是固体，经过一系列保护-脱保护反应后，可从市售还原糖中以高收率制备。后期TEMPO介导的选择性氧化反应最终导致含有葡糖醛酸单元的五糖。选择2-（4-甲氧基苯氧基）乙基作为端基保护基，以提供与乙二醇连接基连接的三糖和五糖衍生物。
• Corrigendum to “Facile synthesis of a pentasaccharide repeating unit corresponding to the common O-antigen of Salmonella enterica O57 and Escherichia coli O51” [Tetrahedron: Asymmetry 24 (2013) 606–611]
  作者：Tamashree Ghosh、Abhishek Santra、Anup Kumar Misra

  DOI：10.1016/j.tetasy.2013.05.018

  日期：2013.7
• Efficient synthesis of the tetrasaccharide repeating unit of the O-antigen of Escherichia coli O174 strain
  作者：Ishani Bhaumik、Tamashree Ghosh、Anup Kumar Misra

  DOI：10.1016/j.carres.2014.08.003

  日期：2014.11

  The tetrasaccharide repeating unit of the O-antigen of Escherichia coli O174 strain was synthesized applying sequential glycosylations of suitably functionalized monosaccharide intermediates. Activation of glycosyl trichloroacetimidate derivatives using nitrosyl tetrafluoroborate (NOBF4) has been used during the synthesis. The glycosylation steps were high yielding with satisfactory stereo outcome. (C) 2014 Elsevier Ltd. All rights reserved.