methyl 2,3,4-tri-O-benzyl-6-(4'-(o-nitrophthalimido)butyryl)-α-D-glucopyranoside | 1085377-61-2

• 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: methyl 2,3,4-tri-O-benzyl-6-(4'-(o-nitrophthalimido)butyryl)-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl 4-(4-nitro-1,3-dioxoisoindol-2-yl)butanoate
• CAS: 1085377-61-2
• 化学式: C₄₀H₄₀N₂O₁₁
• 分子量: 724.764
• InChiKey: DENFIOYWEDQJJA-YXGPIVSISA-N

物化性质

• 沸点：
  826.3±65.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  53
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  156
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-(4'-(o-nitrophthalimido)butyryl)-α-D-glucopyranoside 在 乙酸肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以99%的产率得到甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Protecting-Group-Based Colorimetric Monitoring of Fluorous-Phase and Solid-Phase Synthesis of Oligoglucosamines

  摘要：

  A new hydroxyl protecting group, nitrophthalimidobutyric (NPB) acid, has been synthesized in one solvent-free step for colorimetric monitoring of reaction cycles upon its facile removal with hydrazine acetate in the solid-phase and fluorous-phase syntheses of antigenic oligoglucosamines associated with infectious Staphylococcus aureus. The NPB group serves as a convenient hydroxyl protecting group that is stable to the basic conditions required for the synthesis of the common trichloroacetimidate protecting groups, the strongly acidic conditions used in glycosylation reactions, as well as conditions commonly used to remove silicon-based protecting groups.

  DOI：

  10.1021/ol802229b
• 作为产物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 4-(o-nitrophthalimido)butyric acid 在 吡啶 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到methyl 2,3,4-tri-O-benzyl-6-(4'-(o-nitrophthalimido)butyryl)-α-D-glucopyranoside
  参考文献：
  名称：

  Protecting-Group-Based Colorimetric Monitoring of Fluorous-Phase and Solid-Phase Synthesis of Oligoglucosamines

  摘要：

  A new hydroxyl protecting group, nitrophthalimidobutyric (NPB) acid, has been synthesized in one solvent-free step for colorimetric monitoring of reaction cycles upon its facile removal with hydrazine acetate in the solid-phase and fluorous-phase syntheses of antigenic oligoglucosamines associated with infectious Staphylococcus aureus. The NPB group serves as a convenient hydroxyl protecting group that is stable to the basic conditions required for the synthesis of the common trichloroacetimidate protecting groups, the strongly acidic conditions used in glycosylation reactions, as well as conditions commonly used to remove silicon-based protecting groups.

  DOI：

  10.1021/ol802229b

文献信息

• Protecting-Group-Based Colorimetric Monitoring of Fluorous-Phase and Solid-Phase Synthesis of Oligoglucosamines
  作者：Kwang-Seuk Ko、Gisun Park、Yang Yu、Nicola L. Pohl

  DOI：10.1021/ol802229b

  日期：2008.12.4

  A new hydroxyl protecting group, nitrophthalimidobutyric (NPB) acid, has been synthesized in one solvent-free step for colorimetric monitoring of reaction cycles upon its facile removal with hydrazine acetate in the solid-phase and fluorous-phase syntheses of antigenic oligoglucosamines associated with infectious Staphylococcus aureus. The NPB group serves as a convenient hydroxyl protecting group that is stable to the basic conditions required for the synthesis of the common trichloroacetimidate protecting groups, the strongly acidic conditions used in glycosylation reactions, as well as conditions commonly used to remove silicon-based protecting groups.