p-methoxyphenyl 3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranosyl(1→3)-4,6-O-benzylidene-2-O-benzyl-β-D-glucopyranoside | 1535966-48-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranosyl(1→3)-4,6-O-benzylidene-2-O-benzyl-β-D-glucopyranoside
• CAS: 1535966-48-3
• 化学式: C₄₉H₅₁ClO₁₂
• 分子量: 867.39
• InChiKey: YXYUYZUMCAFYGW-XSZGSVTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.95
• 重原子数：
  62.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  118.6
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranosyl(1→3)-4,6-O-benzylidene-2-O-benzyl-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 溶剂黄146 、 lanthanum(lll) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 p-methoxyphenyl 3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranosyl(1→3)-2-O-benzyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of two trisaccharides related to the hepatoprotective phenylethanoids leonoside E and F isolated from Leonurus japonicus Houtt

  摘要：

  The chemical synthesis of two trisaccharides related to leonoside E and F is reported. The target oligosaccharides were prepared in the form of their p-methoxyphenyl glycosides using a common disaccharide acceptor. All reaction steps were high yielding (>80%) and the stereoselective glycosylations were achieved by activation of the thioglycoside donors using N-iodosuccinimide in the presence of La(OTf)(3). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.014
• 作为产物：
  描述：

  在 N-碘代丁二酰亚胺 、 cesium fluoride 、 lanthanum(lll) triflate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 p-methoxyphenyl 3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranosyl(1→3)-4,6-O-benzylidene-2-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of two trisaccharides related to the hepatoprotective phenylethanoids leonoside E and F isolated from Leonurus japonicus Houtt

  摘要：

  The chemical synthesis of two trisaccharides related to leonoside E and F is reported. The target oligosaccharides were prepared in the form of their p-methoxyphenyl glycosides using a common disaccharide acceptor. All reaction steps were high yielding (>80%) and the stereoselective glycosylations were achieved by activation of the thioglycoside donors using N-iodosuccinimide in the presence of La(OTf)(3). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.014