4-methoxyphenyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-[4-O-benzyl-2-O-(4-methoxybenzyl)-α-L-rhamnopyranosyl]-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranoside | 1253267-70-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-[4-O-benzyl-2-O-(4-methoxybenzyl)-α-L-rhamnopyranosyl]-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranoside
• CAS: 1253267-70-7
• 化学式: C₆₉H₇₁NO₁₇
• 分子量: 1186.32
• InChiKey: WJSSVZDOYKUVSG-HGHLKGIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.55
• 重原子数：
  87.0
• 可旋转键数：
  22.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  186.83
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-[4-O-benzyl-2-O-(4-methoxybenzyl)-α-L-rhamnopyranosyl]-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranoside 、 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 0.75h， 以81%的产率得到4-methoxyphenyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-[4-O-benzyl-2-O-(4-methoxybenzyl)-α-L-rhamnopyranosyl]-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-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
• 作为产物：
  描述：

  4-methoxyphenyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-[4-O-benzyl-2-O-(4-methoxybenzyl)-α-L-rhamnopyranosyl]-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 0.5h， 以98%的产率得到4-methoxyphenyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-[4-O-benzyl-2-O-(4-methoxybenzyl)-α-L-rhamnopyranosyl]-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-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