(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-glucopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-2-O-(4-methoxybenzyl)-D-myo-inositol | 851620-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-glucopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-2-O-(4-methoxybenzyl)-D-myo-inositol
• CAS: 851620-19-4
• 化学式: C₅₈H₆₁N₃O₁₁
• 分子量: 976.136
• InChiKey: XOUUMJVQYUPMBY-YGIACOOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.41
• 重原子数：
  72.0
• 可旋转键数：
  23.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  150.29
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-glucopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-2-O-(4-methoxybenzyl)-D-myo-inositol 在 盐酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以43%的产率得到(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-1-O-allyl-3,5-di-O-benzyl-2-O-(4-methoxybenzyl)-D-myo-inositol
  参考文献：
  名称：

  Convergent Synthesis of a Fully Lipidated Glycosylphosphatidylinositol Anchor of Plasmodium falciparum

  摘要：

  A highly convergent strategy for the synthesis of fully lipidated GPI anchors of malarial origin is reported. This strategy utilized three orthogonal protecting groups, which can be chemoselectively deprotected and functionalized in the late stage of the synthesis. Rapid access to the target GPIs in a highly efficient manner in sufficient quantities for the biological studies has been achieved.

  DOI：

  10.1021/ja042374o
• 作为产物：
  描述：

  (2-azido-2-deoxy-α,β-D-glucopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-2-O-(4-methoxybenzyl)-D-myo-inositol 在 四丁基碘化铵 、 sodium hydride 、 (+)-10-camphorsulfonic acid 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 9.33h， 生成 (2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-glucopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-2-O-(4-methoxybenzyl)-D-myo-inositol
  参考文献：
  名称：

  Convergent Synthesis of a Fully Lipidated Glycosylphosphatidylinositol Anchor of Plasmodium falciparum

  摘要：

  A highly convergent strategy for the synthesis of fully lipidated GPI anchors of malarial origin is reported. This strategy utilized three orthogonal protecting groups, which can be chemoselectively deprotected and functionalized in the late stage of the synthesis. Rapid access to the target GPIs in a highly efficient manner in sufficient quantities for the biological studies has been achieved.

  DOI：

  10.1021/ja042374o