bis(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosid-6-yl)amine | 887624-14-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosid-6-yl)amine
• 英文别名: 1-[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]-N-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl]methanamine
• CAS: 887624-14-8
• 化学式: C₅₆H₆₃NO₁₀
• 分子量: 910.117
• InChiKey: PLWLBYZSVAZVMB-AOTKYVILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  67
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  bis(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosid-6-yl)amine 在 palladium on activated charcoal 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 (R)-12-Hydroxy-octadecanoic acid bis-((2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-amide
  参考文献：
  名称：

  Synthesis of New Sugar-Based Surfactants and Evaluation of Their Hemolytic Activities

  摘要：

  The synthesis of four sugar-based surfactants derived from glucose and (R)-12-hydroxystearic acid is described. The surfactants have a hydroxy group in the hydrophobic part, which is either free or acylated using acetyl chloride, hexanoyl chloride, or myristoyl chloride. Three of the synthesized surfactants are water-soluble and are evaluated with respect to their CMCs and hemolytic activities. The fourth surfactant has limited water solubility and is not further included in the study. The investigated surfactants are all hemolytic close to their respective CMC indicating that their use in parenteral formulations may be limited. Nevertheless, surfactants having the proposed structure appear as promising alternatives to existing solubilizing agents for pharmaceutical applications.

  DOI：

  10.1021/jo051904b
• 作为产物：
  描述：

  methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 titanium(IV) isopropylate 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 51.0h， 生成 bis(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosid-6-yl)amine
  参考文献：
  名称：

  Synthesis of New Sugar-Based Surfactants and Evaluation of Their Hemolytic Activities

  摘要：

  The synthesis of four sugar-based surfactants derived from glucose and (R)-12-hydroxystearic acid is described. The surfactants have a hydroxy group in the hydrophobic part, which is either free or acylated using acetyl chloride, hexanoyl chloride, or myristoyl chloride. Three of the synthesized surfactants are water-soluble and are evaluated with respect to their CMCs and hemolytic activities. The fourth surfactant has limited water solubility and is not further included in the study. The investigated surfactants are all hemolytic close to their respective CMC indicating that their use in parenteral formulations may be limited. Nevertheless, surfactants having the proposed structure appear as promising alternatives to existing solubilizing agents for pharmaceutical applications.

  DOI：

  10.1021/jo051904b

文献信息

• Iridium-catalysed condensation of alcohols and amines as a method for aminosugar synthesis
  作者：Ian Cumpstey、Santosh Agrawal、K. Eszter Borbas、Belén Martín-Matute

  DOI：10.1039/c1cc12800k

  日期：——

  Primary carbohydrate amines at primary and secondary carbons are alkylated by alcohols in the presence of [Cp*IrCl2]2. When primary carbohydrate alcohols are used as the coupling partners and in the presence of Cs2CO3, amine-linked pseudodisaccharides are obtained. Secondary carbohydrate alcohols are unaffected under these conditions, which allows regioselective reactions.

  在[Cp*IrCl2]2的存在下，初级和次级的碳水化合物氨基会被醇所烷基化。当使用初级碳水化合物醇作为耦合伴侣并在Cs2CO3的存在下，可以得到氨基连接的拟二糖。在这些条件下，次级碳水化合物醇不会受到影响，从而实现了区域选择性反应。
• Synthesis of New Sugar-Based Surfactants and Evaluation of Their Hemolytic Activities
  作者：Kristina Neimert-Andersson、Sven Sauer、Olaf Panknin、Tessie Borg、Erik Söderlind、Peter Somfai

  DOI：10.1021/jo051904b

  日期：2006.4.1

  The synthesis of four sugar-based surfactants derived from glucose and (R)-12-hydroxystearic acid is described. The surfactants have a hydroxy group in the hydrophobic part, which is either free or acylated using acetyl chloride, hexanoyl chloride, or myristoyl chloride. Three of the synthesized surfactants are water-soluble and are evaluated with respect to their CMCs and hemolytic activities. The fourth surfactant has limited water solubility and is not further included in the study. The investigated surfactants are all hemolytic close to their respective CMC indicating that their use in parenteral formulations may be limited. Nevertheless, surfactants having the proposed structure appear as promising alternatives to existing solubilizing agents for pharmaceutical applications.