2-(4-methoxyphenoxy)ethyl 3,4-di-O-benzyl-α-L-rhamnopyranoside | 1253267-85-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-methoxyphenoxy)ethyl 3,4-di-O-benzyl-α-L-rhamnopyranoside
• 英文别名: (2R,3R,4S,5S,6S)-2-[2-(4-methoxyphenoxy)ethoxy]-6-methyl-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 1253267-85-4
• 化学式: C₂₉H₃₄O₇
• 分子量: 494.585
• InChiKey: ZYJYAUUGNVADDR-MXNGYVQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenoxy)ethyl 3,4-di-O-benzyl-α-L-rhamnopyranoside 、 ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到2-(4-methoxyphenoxy)ethyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of penta- and hexasaccharide fragments corresponding to the O-antigen of Escherichia coli O150

  摘要：

  The chemical synthesis of a pentasaccharide and a hexasaccharide corresponding to the O-antigen of Escherichia coli O150 has been achieved using sequential glycosylation and [3+3] block glycosylation strategies. Suitably protected monosaccharide synthons have been prepared from the commercially available reducing sugars and then stereoselectively coupled to give the pentasaccharide and a hexasaccharide in excellent yields. 4-Methoxyphenyl and 2-(4-methoxyphenoxy) ethyl groups have been used as the anomeric-protecting groups in the target pentasaccharide and a hexasaccharide. respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.022
• 作为产物：
  描述：

  、 溴甲苯 在 二正丁基氧化锡 、 四丁基溴化铵 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以5.5 g的产率得到2-(4-methoxyphenoxy)ethyl 3,4-di-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of penta- and hexasaccharide fragments corresponding to the O-antigen of Escherichia coli O150

  摘要：

  The chemical synthesis of a pentasaccharide and a hexasaccharide corresponding to the O-antigen of Escherichia coli O150 has been achieved using sequential glycosylation and [3+3] block glycosylation strategies. Suitably protected monosaccharide synthons have been prepared from the commercially available reducing sugars and then stereoselectively coupled to give the pentasaccharide and a hexasaccharide in excellent yields. 4-Methoxyphenyl and 2-(4-methoxyphenoxy) ethyl groups have been used as the anomeric-protecting groups in the target pentasaccharide and a hexasaccharide. respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.022

文献信息

• Synthesis of penta- and hexasaccharide fragments corresponding to the O-antigen of Escherichia coli O150
  作者：Rajib Panchadhayee、Anup Kumar Misra

  DOI：10.1016/j.tetasy.2010.06.022

  日期：2010.9

  The chemical synthesis of a pentasaccharide and a hexasaccharide corresponding to the O-antigen of Escherichia coli O150 has been achieved using sequential glycosylation and [3+3] block glycosylation strategies. Suitably protected monosaccharide synthons have been prepared from the commercially available reducing sugars and then stereoselectively coupled to give the pentasaccharide and a hexasaccharide in excellent yields. 4-Methoxyphenyl and 2-(4-methoxyphenoxy) ethyl groups have been used as the anomeric-protecting groups in the target pentasaccharide and a hexasaccharide. respectively. (C) 2010 Elsevier Ltd. All rights reserved.