N-[(2R,4aR,6R,7R,8R,8aS)-6-[8-(4-Methoxy-phenoxy)-octyloxy]-2-phenyl-8-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide | 178986-46-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2R,4aR,6R,7R,8R,8aS)-6-[8-(4-Methoxy-phenoxy)-octyloxy]-2-phenyl-8-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide
• CAS: 178986-46-4
• 化学式: C₆₄H₇₅NO₁₃
• 分子量: 1066.3
• InChiKey: SHHRCNPQQRKRLF-JPROKJPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.86
• 重原子数：
  78.0
• 可旋转键数：
  29.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  139.86
• 氢给体数：
  1.0
• 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-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以90%的产率得到N-[(2R,4aR,6R,7R,8R,8aS)-6-[8-(4-Methoxy-phenoxy)-octyloxy]-2-phenyl-8-((2S,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
• 作为产物：
  描述：

  8-p-methoxyphenoxyloctanol 在 甲醇 、 calcium sulfate 、 sodium methylate 、 silver trifluoromethanesulfonate 、 氰化汞 、 对甲苯磺酸 、 silver carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 生成 N-[(2R,4aR,6R,7R,8R,8aS)-6-[8-(4-Methoxy-phenoxy)-octyloxy]-2-phenyl-8-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-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