6-Benzyloxycarbonylaminohexyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside | 213194-02-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-Benzyloxycarbonylaminohexyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
• CAS: 213194-02-6
• 化学式: C₄₈H₄₇NO₁₂
• 分子量: 829.901
• InChiKey: NPQODUSTGLIBSK-KPAAGLOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.75
• 重原子数：
  61.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  161.99
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  6-Benzyloxycarbonylaminohexyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以100%的产率得到6-Benzyloxycarbonylaminohexyl β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Oligosaccharide Dendrimers

  摘要：

  Two beta-D-glucopyranoside-based dendrimers, one incorporating three tetra- and the other three heptasaccharide wedges attached to a central trisfunctionalized nonsaccharide core component, have been synthesized. Branching at designated saccharide units of the tetra- and of the heptasaccharide wedges arises from (1-->2)/(1-->3)/(1-->6) and from (1-->3)/(1-->6) intersaccharide linkages, respectively with the 1,2-trans configuration at all anomeric centers. Both oligosaccharide wedges were constructed by stepwise glycosylation strategies and have reactive primary amino groups at their focal points located at the termini of spacer arms connected to the reducing glucose residues. Amide bond formation be tween these amino groups and appropriate core components carrying three carboxylic acid functions afforded two dendrimers incorporating a total of 12 and 21 monosaccharide units when the tetra- and the heptasaccharide wedges were employed, respectively, These nanosized highly branched macromolecules possess molecular diameters of 5-6 nm and molecular weights of 6195 and 10 008 Daltons for the 12-mer and 21-mer, respectively. The wedges and dendrimers were characterized and the intersaccharide connectivity elucidated by extensive mono- and bidimensional H-1 and C-13 NMR spectroscopic investigations. In addition, LSIMS and MALDI-TOFMS investigations were also performed and revealed molecular ion peaks generally as H, Na. or K adducts for all oligosaccharides.

  DOI：

  10.1002/(sici)1521-3765(19980710)4:7<1244::aid-chem1244>3.0.co;2-8
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoylglucosyl bromide 、 6-(Z-氨基)-1-己醇 在 4 A molecular sieve 、 氰化汞 、 mercury dibromide 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到6-Benzyloxycarbonylaminohexyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Oligosaccharide Dendrimers

  摘要：

  Two beta-D-glucopyranoside-based dendrimers, one incorporating three tetra- and the other three heptasaccharide wedges attached to a central trisfunctionalized nonsaccharide core component, have been synthesized. Branching at designated saccharide units of the tetra- and of the heptasaccharide wedges arises from (1-->2)/(1-->3)/(1-->6) and from (1-->3)/(1-->6) intersaccharide linkages, respectively with the 1,2-trans configuration at all anomeric centers. Both oligosaccharide wedges were constructed by stepwise glycosylation strategies and have reactive primary amino groups at their focal points located at the termini of spacer arms connected to the reducing glucose residues. Amide bond formation be tween these amino groups and appropriate core components carrying three carboxylic acid functions afforded two dendrimers incorporating a total of 12 and 21 monosaccharide units when the tetra- and the heptasaccharide wedges were employed, respectively, These nanosized highly branched macromolecules possess molecular diameters of 5-6 nm and molecular weights of 6195 and 10 008 Daltons for the 12-mer and 21-mer, respectively. The wedges and dendrimers were characterized and the intersaccharide connectivity elucidated by extensive mono- and bidimensional H-1 and C-13 NMR spectroscopic investigations. In addition, LSIMS and MALDI-TOFMS investigations were also performed and revealed molecular ion peaks generally as H, Na. or K adducts for all oligosaccharides.

  DOI：

  10.1002/(sici)1521-3765(19980710)4:7<1244::aid-chem1244>3.0.co;2-8