ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside | 1253268-01-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside
• CAS: 1253268-01-7
• 化学式: C₅₇H₆₃NO₁₉S
• 分子量: 1098.19
• InChiKey: CGIBLZZKSQKHJY-RBZSGLBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  78.0
• 可旋转键数：
  19.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  225.65
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenoxy)ethyl (4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside 、 ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside 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76%的产率得到2-(4-methoxyphenoxy)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl)-(1->2)-(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：

  (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate 、 ETHYL4,6-O-BENZYLIDENE-2-DEOXY-2-PHTHALIMIDO-1-THIO-Β-D-GLUCOPYRANOSIDE乙基4,6-O-亚苄基-2-脱氧-2-邻苯二甲酰亚氨基-1-硫代-Β-D-吡喃葡萄糖苷 在 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75%的产率得到ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside
  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