2-(4-methoxyphenoxy)ethyl 1,2,3,4-tetra-O-acetyl-α-L-rhamnopyranoside | 1253267-81-0

• 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 1,2,3,4-tetra-O-acetyl-α-L-rhamnopyranoside
• 英文别名: 2(p-methoxyphenoxy)ethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranoside
• CAS: 1253267-81-0
• 化学式: C₂₁H₂₈O₁₀
• 分子量: 440.447
• InChiKey: SHNFTDYYIXHIDZ-NWXLSTKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  115.82
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenoxy)ethyl 1,2,3,4-tetra-O-acetyl-α-L-rhamnopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 3.0h， 以5.7 g的产率得到
  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：

  1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 、 2-(4-甲氧基苯氧基)-1-乙醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以87%的产率得到2-(4-methoxyphenoxy)ethyl 1,2,3,4-tetra-O-acetyl-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

• Stereoselective Glycosylations by Nitrosyl Tetrafluoroborate-Catalyzed Activation of Glycosyl Trichloroacetimidate Derivatives
  作者：Anup Misra、Abhijit Sau、Abhishek Santra

  DOI：10.1055/s-0032-1317135

  日期：——

  Efficient stereoselective glycosylation conditions have been developed by using nitrosyl tetrafluoroborate (NOBF4) promoted activation of glycosyl trichloroacetimidate derivatives. A series of mono- and disaccharide derivatives were synthesized in excellent yield, and high stereoselectivity at the glycosylation center was observed in every case.