N-[(2R,4aR,6R,7R,8R,8aS)-6-[8-(4-Methoxy-phenoxy)-octyloxy]-2-phenyl-8-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide | 178986-41-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: N-[(2R,4aR,6R,7R,8R,8aS)-6-[8-(4-Methoxy-phenoxy)-octyloxy]-2-phenyl-8-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide
• CAS: 178986-41-9
• 化学式: C₃₆H₅₁NO₁₃
• 分子量: 705.8
• InChiKey: XLNVDDCAIXGRHH-VAMXGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  50.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  183.86
• 氢给体数：
  5.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  N-[(2R,4aR,6R,7R,8R,8aS)-6-[8-(4-Methoxy-phenoxy)-octyloxy]-2-phenyl-8-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 在 溶剂黄146 作用下， 反应 3.0h， 以80%的产率得到N-[(2R,3R,4R,5S,6R)-5-Hydroxy-6-hydroxymethyl-2-[8-(4-methoxy-phenoxy)-octyloxy]-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Towards oligosaccharide libraries: A study of the random galactosylation of unprotected N-acetylglucosamine

  摘要：

  A single reaction of an unprotected beta-D-GlcNAc glycoside with tetra-O-acetyl-alpha-D-galactopyranosyl trichloroacetimidate in dioxane, catalyzed by BF3-etherate, was shown to yield all six possible Gal-GlcNAc disaccharides. This result is surprising not only because significant amounts of alpha-linked disaccharides were formed, despite the presence of a participating group at O-2 of the glycosyl donor, but also because glycosylation of the primary OH-6 is not the dominant reaction. These results suggest 'random-glycosylation' to be a valid strategy for the rapid production of oligosaccharide libraries. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0968-0896(96)00064-8
• 作为产物：
  描述：

  8-p-methoxyphenoxyloctanol 在 甲醇 、 calcium sulfate 、 sodium methylate 、 氰化汞 、 对甲苯磺酸 作用下， 以 硝基甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 40.0h， 生成 N-[(2R,4aR,6R,7R,8R,8aS)-6-[8-(4-Methoxy-phenoxy)-octyloxy]-2-phenyl-8-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide
  参考文献：
  名称：

  Towards oligosaccharide libraries: A study of the random galactosylation of unprotected N-acetylglucosamine

  摘要：

  A single reaction of an unprotected beta-D-GlcNAc glycoside with tetra-O-acetyl-alpha-D-galactopyranosyl trichloroacetimidate in dioxane, catalyzed by BF3-etherate, was shown to yield all six possible Gal-GlcNAc disaccharides. This result is surprising not only because significant amounts of alpha-linked disaccharides were formed, despite the presence of a participating group at O-2 of the glycosyl donor, but also because glycosylation of the primary OH-6 is not the dominant reaction. These results suggest 'random-glycosylation' to be a valid strategy for the rapid production of oligosaccharide libraries. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0968-0896(96)00064-8