Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-((R)-2,3-bis-hexadecyloxy-propoxy)-6-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester | 677008-57-0

• 英文名称: Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-((R)-2,3-bis-hexadecyloxy-propoxy)-6-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester
• CAS: 677008-57-0
• 化学式: C₆₁H₁₀₆O₂₀
• 分子量: 1159.5
• InChiKey: SADHZHODZXRIFB-SFLWEUCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.99
• 重原子数：
  81.0
• 可旋转键数：
  47.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  239.48
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-((R)-2,3-bis-hexadecyloxy-propoxy)-6-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以77%的产率得到
  参考文献：
  名称：

  Influence of Subphase Conditions on Interfacial Viscoelastic Properties of Synthetic Lipids with Gentiobiose Head Groups

  摘要：

  The thermodynamic parameters and rheological properties of a synthetic glycolipid with a gentiobiose (O(beta-D-glucopyranosyl)-(1-->6-beta-D-glucopyranoside)) headgroup have been studied at the air/water interface. The phase transition entropy and latent heat were estimated by film balance experiments at various temperatures, whereas dynamic surface moduli (loss and storage modulus) were measured by an interfacial stress rheometer under well-defined thermodynamic conditions. The impact of glucosidic bonding was systematically studied by comparing the measured results to those from the lipid with a lactose (O-(beta-D-galactopyranosyl)-(1-->4-beta-D-glucopyranoside)) headgroup, which possesses the similar monosaccharide composition. We found that the "bent" 1-->6 junction of gentiobiose reduces the lateral intermolecular cooperativity and fluidizes the films in comparison to the lactose lipid monolayer.

  DOI：

  10.1021/jp0367934
• 作为产物：
  描述：

  gentiobiose hepta-acetate 在 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-((R)-2,3-bis-hexadecyloxy-propoxy)-6-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Influence of Subphase Conditions on Interfacial Viscoelastic Properties of Synthetic Lipids with Gentiobiose Head Groups

  摘要：

  The thermodynamic parameters and rheological properties of a synthetic glycolipid with a gentiobiose (O(beta-D-glucopyranosyl)-(1-->6-beta-D-glucopyranoside)) headgroup have been studied at the air/water interface. The phase transition entropy and latent heat were estimated by film balance experiments at various temperatures, whereas dynamic surface moduli (loss and storage modulus) were measured by an interfacial stress rheometer under well-defined thermodynamic conditions. The impact of glucosidic bonding was systematically studied by comparing the measured results to those from the lipid with a lactose (O-(beta-D-galactopyranosyl)-(1-->4-beta-D-glucopyranoside)) headgroup, which possesses the similar monosaccharide composition. We found that the "bent" 1-->6 junction of gentiobiose reduces the lateral intermolecular cooperativity and fluidizes the films in comparison to the lactose lipid monolayer.

  DOI：

  10.1021/jp0367934