5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside | 219791-69-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(6-methoxy-6-oxohexoxy)oxan-2-yl]methyl benzoate
• CAS: 219791-69-2
• 化学式: C₄₁H₄₀O₁₂
• 分子量: 724.761
• InChiKey: KJYVZOCKIFBJPY-HXLYXAJGSA-N

物化性质

• 沸点：
  796.195±60.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.311±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  53
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 以 乙醇 为溶剂， 反应 36.0h， 生成 N-[2-[(2-ethoxy-3,4-dioxocyclobuten-1-yl)amino]ethyl]-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanamide
  参考文献：
  名称：

  Studies towards neoglycoconjugates from the monosaccharide determinant of Vibrio cholerae O:1, serotype Ogawa using the diethyl squarate reagent

  摘要：

  The effect of reaction time, concentration and molar excess of hapten upon the efficiency of the conjugation of carbohydrates to proteins using the diethyl squarate reagent has been studied using chicken serum albumin (CSA) as the carrier protein and a linker-equipped D-glucose derivative as the hapten. A high degree of incorporation of the latter into CSA was achieved with high efficiency, and the use of a large excess of the ligand was not necessary. Conjugation of the immunodominant monosaccharide determinant of Vibrio cholerae O:1, serotype Ogawa, bearing the same spacer, followed a similar pattern, showing that the nature of the carbohydrate does not substantially affect the outcome of the conjugation and that a predicted degree of antigen-loading onto carrier protein is possible to achieve. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00261-4
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoylglucosyl bromide 、 6-羟基己酸甲酯 在 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 甲苯 为溶剂， 反应 30.0h， 以77%的产率得到5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Studies towards neoglycoconjugates from the monosaccharide determinant of Vibrio cholerae O:1, serotype Ogawa using the diethyl squarate reagent

  摘要：

  The effect of reaction time, concentration and molar excess of hapten upon the efficiency of the conjugation of carbohydrates to proteins using the diethyl squarate reagent has been studied using chicken serum albumin (CSA) as the carrier protein and a linker-equipped D-glucose derivative as the hapten. A high degree of incorporation of the latter into CSA was achieved with high efficiency, and the use of a large excess of the ligand was not necessary. Conjugation of the immunodominant monosaccharide determinant of Vibrio cholerae O:1, serotype Ogawa, bearing the same spacer, followed a similar pattern, showing that the nature of the carbohydrate does not substantially affect the outcome of the conjugation and that a predicted degree of antigen-loading onto carrier protein is possible to achieve. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00261-4