6-Benzyloxycarbonylaminohexyl β-D-glucopyranoside | 213194-03-7

• 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 β-D-glucopyranoside
• 英文别名: 6-N-benzyloxycarbonylamino-hexyl β-D-glucopyranoside
• CAS: 213194-03-7
• 化学式: C₂₀H₃₁NO₈
• 分子量: 413.468
• InChiKey: XNJPRGYOVBDSRW-UJWQCDCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.29
• 重原子数：
  29.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  137.71
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6-Benzyloxycarbonylaminohexyl β-D-glucopyranoside 在 D(+)-10-樟脑磺酸 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0~50.0 ℃ 、666.61 Pa 条件下， 反应 76.0h， 生成 6-Benzyloxycarbonylaminohexyl 2-O-benzoyl-4,6-O-benzylidene-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 在 4 A molecular sieve 、 sodium methylate 、 氰化汞 、 mercury dibromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 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

文献信息

• [EN] HEPARAN SULFATE GLYCOMIMETIC COMPOUNDS AND THEIR PHARMACEUTICAL AND COSMECEUTICAL USES<br/>[FR] COMPOSÉS GLYCOMIMÉTIQUES DE SULFATE D'HÉPARANE ET LEURS UTILISATIONS PHARMACEUTIQUES ET COSMÉTIQUES
  申请人：VICTORIA LINK LTD

  公开号：WO2018174725A1

  公开（公告）日：2018-09-27

  The invention relates to dendritic compounds, the use of these compounds as pharmaceuticals, pharmaceutical and cosmeceutical compositions containing the compounds, and methods of treating cancer, inflammation, diabetic nephropathy, neurodegenerative disorders, Niemann-Pick Type C disease, or dermatological conditions.

  该发明涉及树枝状化合物，这些化合物作为药物的使用，包含这些化合物的药物和美容药物组合物，以及治疗癌症、炎症、糖尿病肾病、神经退行性疾病、尼曼-皮克病C型或皮肤病学状况的方法。